Hydrochloric Acid → HCID 19092862, compound

HRID 487660Notes

Reaction equation

HRID 487660 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([C:14]([O:16]C)=[O:15])=[C:6]2[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1.[OH-].[Na+].CO.Cl>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([C:14]([OH:16])=[O:15])=[C:6]2[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 9842367HCID 9842367, compound

Product 1

HCID 19092862HCID 19092862, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 5,6-dimethoxy-3-(3,4-dimethoxyphenyl)indole-2-carboxylate (0.54 g), 2N-NaOH (10 ml) and methanol (25 ml) was refluxed for 3 hours under stirring. The reaction mixture was poured into water, acidified with 6N-HCl and extracted with chloroform. The chloroform layer was washed with water, dried (MgSO4) and concentrated. The precipitated crystals were collected by filtration and recrystallized from methanol to give 5,6-dimethoxy-3-(3,4-dimethoxyphenyl)indole-2-carboxylic acid (0.443 g, 85%) as pale red prisms.

Workup

  1. temperaturewas refluxed for 3 hours
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. filtrationThe precipitated crystals were collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e1ded70f95724e6799565740be01ab7c
Source dataset
uspto-grants-1994_03
Patent number
US05296499

Reaction notes

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