Hydrochloric Acid → (S)-N-(alpha-ethylbenzyl)-3-(carboxymethoxy)-2-phenylquinoline-4-carboxamide hydrochloride

HRID 651059Notes

Reaction equation

HRID 651059 reaction equation
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[O:29][CH2:30][C:31]([O:33]CC)=[O:32])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[ClH:36]>>[ClH:36].[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[O:29][CH2:30][C:31]([OH:33])=[O:32])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 10790452(S)-N-(alpha-ethylbenzyl)-3-(ethoxycarbonylmethoxy)-2-phenylquinoline-4-carboxamide2×

Product 1

HCID 9891183(S)-N-(alpha-ethylbenzyl)-3-(carboxymethoxy)-2-phenylquinoline-4-carboxamide hydrochloride

Procedure

0.35 g (0.7 mmol) of (S)-N-(α-ethylbenzyl)-3-(ethoxycarbonylmethoxy)-2-phenyl quinoline-4-carboxamide (compound of Example 1) were dissolved in 20 ml of 37% HCl and the reaction mixture was refluxed under magnetical stirring for 20′. The solution was evaporated in-vacuo to dryness and the crude product was triturated with warm EtOAc/i-PrOH to yield 0.17 g of the title compound as a white solid.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. customThe solution was evaporated in-vacuo to dryness
  3. customthe crude product was triturated with warm EtOAc/i-PrOH

Sources & evidence

ORD record
ord-e576d9c2070544e1af5d3dee462af122
Source dataset
uspto-grants-2001_08
Patent number
US06277862B1

Reaction notes

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