Water → HCID 13220402, compound

HRID 1649853Notes

Reaction equation

HRID 1649853 reaction equation
COC([C:5]1[O:16][C:15]2[C:14]3[CH:13]=[C:12]([O:17][CH3:18])[CH:11]=[CH:10][C:9]=3[N:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]=2[C:6]=1[OH:25])=O.O.[OH-].[Na+]>CN(C)C=O>[CH3:18][O:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]3[C:6](=[O:25])[CH2:5][O:16][C:15]=3[C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54723453HCID 54723453, compound

Product 1

HCID 13220402HCID 13220402, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 39.0 g (0.12 mole) of 3-hydroxy-7-methoxy-4-phenyl-4H-furo[3,2-b]indole-2-carboxylic methyl ester (Preparation described in U.S. Pat. Application Serial Number 369,448 now issued as U.S. Pat. No. 4,503,236) in 195 ml of N,N-dimethylformamide and 80 ml of water was treated with 40 ml of 50% aqueous sodium hydroxide, After heating on the steam bath for two hours, the product was isolated as described in Example V above. Recrystallization from 2-methoxyethanol/N,N-dimethylformamide yielded 15.8 g (49% yield) of the product, mp 175° C.-dec. An additional recrystallization as above raised the mp to 185°-187° C.

Workup

  1. customPreparation
  2. temperatureAfter heating on the steam bath for two hours
  3. customthe product was isolated
  4. customRecrystallization from 2-methoxyethanol/N,N-dimethylformamide

Sources & evidence

ORD record
ord-0bdf1e158e4c4c8e83501a252fc60d19
Source dataset
uspto-grants-1990_05
Patent number
US04921871

Reaction notes

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