Methanol → 2-(Indol-3-yl)-4-carboxy-6,7-dimethoxyquinoline

HRID 582431Notes

Reaction equation

HRID 582431 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[CH:28]=[C:27]([C:29]([OH:31])=[O:30])[C:26]4[C:21](=[CH:22][C:23]([O:34][CH3:35])=[C:24]([O:32][CH3:33])[CH:25]=4)[N:20]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CO>O>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[CH:28]=[C:27]([C:29]([OH:31])=[O:30])[C:26]3[C:21](=[CH:22][C:23]([O:34][CH3:35])=[C:24]([O:32][CH3:33])[CH:25]=3)[N:20]=2)=[CH:11]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 187886132-(N-phenylsulfonylindol-3-yl)-4-carboxy-6,7-dimethoxyquinoline

Product 1

HCID 187887092-(Indol-3-yl)-4-carboxy-6,7-dimethoxyquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of (0.547 g) of 2-(N-phenylsulfonylindol-3-yl)-4-carboxy-6,7-dimethoxyquinoline, K2CO3 (0.380 g), MeOH (40 ml) and H2O (10 ml) are heated to reflux. The MeOH is evaporated in vacuo, and the aqueous residue diluted with more H2O, and acidified with 0.IN HCl to pH between 6°-7 while contained in an ice-bath. An orange solid precipitates. This is collected, washed with ether then dried under vacuum (0.1 mm at 22° C.) for a few hours to obtain 2-(indol-3-yl)-4-carboxy-6,7-dimethoxyquinoline m.p. 286° C. dec).

Workup

  1. customThe MeOH is evaporated in vacuo
  2. additionthe aqueous residue diluted with more H2O
  3. customto pH between 6°
  4. customwhile contained in an ice-bath
  5. customAn orange solid precipitates
  6. customThis is collected
  7. washwashed with ether
  8. customthen dried under vacuum (0.1 mm at 22° C.) for a few hours

Sources & evidence

ORD record
ord-45e27e896a2540d88e0893246939c8c5
Source dataset
uspto-grants-1999_07
Patent number
USRE036256

Reaction notes

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