Acetyl chloride → 1-{4-[2-(2-Methoxycarbonylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline

HRID 441250Notes

Reaction equation

HRID 441250 reaction equation
[C:1](Cl)(=O)C.[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:40]=[CH:39][CH:38]=[CH:37][C:15]=1[C:16]([NH:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1)=[O:17])([OH:7])=[O:6]>CO>[CH3:1][O:6][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:40]=[CH:39][CH:38]=[CH:37][C:15]=1[C:16]([NH:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1)=[O:17])=[O:7]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 224051021-{4-[2-(2-Carboxyphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline

Product 1

HCID 224051041-{4-[2-(2-Methoxycarbonylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetyl chloride (1 ml) and methanol (20 ml) was added 1-{4-[2-(2-carboxyphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (350 mg) at 0° C. The solution was stirred for 30 minutes at the same temperature and then stirred for 3 hours at ambient temperature. The solvent was evaporated in vacuo and triturated from dichloromethane to give 1-{4-[2-(2methoxycarbonylphenyl)benzoylamino]benzoyl}-1,2,3,4tetrahydroquinoline (300 mg).

Workup

  1. stirringstirred for 3 hours at ambient temperature
  2. customThe solvent was evaporated in vacuo
  3. customtriturated from dichloromethane

Sources & evidence

ORD record
ord-b91b83a11fe5413b864323bcfbfb8788
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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