Sodium Hydroxide → HCID 19607913, compound

HRID 1603090Notes

Reaction equation

HRID 1603090 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[C:8]([NH:10][C:11]1[CH:28]=[CH:27][C:14]([C:15]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:13][CH:12]=1)=[O:9])(=O)C.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[C:8]([NH:10][C:11]1[CH:28]=[CH:27][C:14]([C:15]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:13][CH:12]=1)=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19607824HCID 19607824, compound

Product 1

HCID 19607913HCID 19607913, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[4-(3-acetyloxybenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (1.5 g) in methanol (20 ml) is added 5% aqueous sodium hydroxide solution (10 ml) and the mixture is stirred at room temperature overnight. Methanol is distilled off under reduced pressure and the resulting residue is acidified with diluted aqueous hydrochloric acid solution. The precipitated crystal is collected by filtration and recrystallized from methanol to give 1-[4-(3-hydroxybenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (1.22 g) as white powder, m.p. 217-218° C.

Workup

  1. distillationMethanol is distilled off under reduced pressure
  2. filtrationThe precipitated crystal is collected by filtration
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-32bfd709e55d4e59bbe7a19093dabefb
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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