8-(2-Methoxyphenyl)-6-methyl-2-(1-methyl-1H-benzo[d]imidazol-2-yl)quinoline

Round 1

Reviewer 1 Report

Lyapchev and co-workers describe the synthesis of 8-(2-methoxyphenyl)-6-methyl-2-(1-methyl-1H- 2 benzo[d]imidazol-2-yl)quinoline in this manuscript. The synthesis is straightforward, but I would like to know the reaction yields without having to look in the experimental. Yields should be in the reaction schemes.

The crystal structure and the UV-VIS spectra are good.

In the experimental procedure for the preparation of 3, the sentence "The solution was washed with diethyl ether (80 mL)" is unclear. Is this a separation?

In the HRMS data, the calculated mass should be of [M-H]+ rather than [M+H] as the cation is what is observed. The ppm difference will then be different in each case.

Otherwise all the data looks good. 

Author Response

We thank the Reviewer for the valuable comments and suggestions, which we have addressed carefully in the response below.

Comments 1: Lyapchev and co-workers describe the synthesis of 8-(2-methoxyphenyl)-6-methyl-2-(1-methyl-1H- 2 benzo[d]imidazol-2-yl)quinoline in this manuscript. The synthesis is straightforward, but I would like to know the reaction yields without having to look in the experimental. Yields should be in the reaction schemes.

Response 1: Yields of the synthesized compounds were added in Schemes 1-3. For clarity, where corrections are made, the changed schemes are highlighted in yellow. 

Comments 2: In the experimental procedure for the preparation of 3, the sentence "The solution was washed with diethyl ether (80 mL)" is unclear. Is this a separation?

Response 2: Washing a solution is a common technique, similar to liquid-liquid extraction. There is little difference - in this case not the valuable component is transferred from phase to phase, but the impurities.

The avoid misconception, the phrase "The solution was washed with diethyl ether (80 mL)" was replaced with "The solution was transferred in separatory funnel and 80 mL of diethyl ether was added. The funnel was shaken vigorously and after 5 minutes the organic layer was discarded." in the experimental procedure of our manuscript. In the next sentence "The crude reaction mixture" was replaced with "The aqueous layer".

For clarity, where corrections are made, the changed text is highlighted in yellow. 

Comments 3: In the HRMS data, the calculated mass should be of [M-H]+ rather than [M+H] as the cation is what is observed. The ppm difference will then be different in each case.

Response 3: The used formula, [M+H]⁺, is correct.

All of the HRMS-analyzed compounds own at least one basic nitrogen atom. During the HRMS studies, one basic nitrogen atom per molecule was protonated, leading to the formation of positively charged [M+H] ion. On the other hand, if a molecule lost a proton, the resulting [M-H] ion will be negatively charged. However, this is unlikely, because the studied molecules do not possess acidic hydrogen atoms.      

Some technical mistakes were corrected as well. They were also highlighted in yellow.    

Round 2

Reviewer 1 Report

The authors have attended to the issues raised.