Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline
Round 1
Reviewer 1 Report
Comments and Suggestions for Authors Manuscript Number: molbank-2926595The manuscript of Deiby F. Aparicio Acevedo, Marlyn C. Ortiz Villamizar, and Vladimir V. Kouznetsov “Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline” presents studies of synthesis of quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide via three-step procedure from 4,7-dichloroquinoline using N-oxidation reaction/C2-amidation reaction/C4 SNAr reaction. According toScifinder the target compound is a new compound. The authors provide a sufficient characterisation for the target compound with FT-IR, 1H‐, 13C-NMR, DEPT-135°, and ESI-MS techniques. The structural elucidation of the intermediate and the target compounds was given in the results and discussion. Spectra were provided in the supplement materials. The physicochemical parameters of the target compound were also calculated.
This is an interesting and well-written paper that fits nicely into the remit of Molbank. The manuscript readability and structure are good, and the research design is appropriate. However, some important issues need to be added and addressed before publication:
3. Materials and Methods 3.1. Chemical Analysis
-Please describe the used equipment and materials according to MDPI style (model, make, City, Country) and the sources of the reagents.
- Is it really necessary to provide the yields of the products in milligrams with numbers after a decimal point? Would it be possible to make rounding to significant figures?
Supplementary materials
- The quality of figures provided in supplementary materials in paragraph 4: ‘’In silico prediction of physicochemical properties’’ can be improved
Consequently, I do recommend accepting this manuscript for publication with minor revision.
Author Response
please see a file
Author Response File: Author Response.pdf
Reviewer 2 Report
Comments and Suggestions for AuthorsThe present manuscript by the Kouznetsov group describes three-step synthesis of the titled compound 4 from commercially available 4,7-dichloroquinoline using conventional (reported) procedure. The reaction sequence is totally accessible and implemented in good to excellent yield. The structure characterization was carefully carried out by using 1H NMR, 13C NMR, IR, MS measurement for new compounds 3 and 4.
A plausible reaction mechanism speculation for the key benzamide formation (2→3) seems to be reasonable.
Physicochemical parameters of the target compound 4 were well-carried out by in silico calculation using SwissADME database.
Thus, the reviewer recommends the publication in Molbank after minor revisions mentioned above and commented below.
<General comments and suggestions>
1. Compound name and number: IUPAC names and the defined names with number: XXXX (##) Generic names with number: YYYY ##. For examples: ethyl acetoacetate (##) and β-ketoester ##. Please check it carefully.
2. Name et al. → Name group or Name’s and coworkers (as a recent style)
<Comments & suggestions>
1. Throughout the study; amidation → amide formation (legitimate technical term)
2. Scheme 1; The sentence, “Three-step ……. (1).” should be deleted, because it is described in the text (repetition).
3. p. 2, line ↑5; and provided → to provide
4. p. 2, line ↑4; “in 2018” should be deleted (meaningless).
5. p. 2, line ↑3; to carry out → to adopt?
6. p. 2, line ↑1; the displacement → the regionselective displacement
7. p. 3, line 3; industrial application → a large-scale production (due to the present stage is R&D)
8. p. 3, <Plausible reaction mechanism>; The tense of sentence is conventionally “present.” The sentence of “Nirinium ion B, ……intermediate D.” is too long (6 lines). Please arrange it.
9. Scheme 2; In intermediate D, two curry arrows are misaligned. Check it.
10. 3.2 Step 1; 172.5 mg → 173 mg (du to the significant figure). Also, Steps 1 and 3: Please check them.
Comments on the Quality of English Languagegenerally acceptable
Author Response
please see a file
Author Response File: Author Response.pdf