Sodium Hydroxide → Y-20811 free acid

HRID 543331Notes

Reaction equation

HRID 543331 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:17][C:3]=1[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]([OH:15])=[O:14])=[CH:8][C:7]=1[CH3:16])=[O:5].[OH-].[Na+].[BH4-].[Na+]>O>[CH3:12][C:11]1[CH:10]=[C:9]([C:13]([OH:15])=[O:14])[CH:8]=[C:7]([CH3:16])[C:6]=1[CH:4]([C:3]1[CH:17]=[C:18]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH:19]=[CH:20][C:2]=1[CH3:1])[OH:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 13850215HCID 13850215, compound

Product 1

HCID 121911Y-20811 free acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 16.2 g of 2-methyl-5-(1-imidazolyl)-2',6'-dimethyl-4'-carboxybenzophenone and 2.1 g of sodium hydroxide in 113 ml of water is added 2.8 g of sodium borohydride, and the mixture is stirred at 70°-75° C. for 3 hours. After completion of the reaction, a small amount of an isoluble substance is filtered off from the warm mixture and the filtrate is adjusted to pH 4 with concentrated hydrochloric acid under stirring at 80°-90° C. The precipitated crystals are collected by filtration under reduced pressure and washed with water well. After drying, recrystallization from dimethylformamide gives 14.0 g of α-(2,6-dimethyl-4-carboxyphenyl)-2-methyl-5-(1-imidazolyl)benzenemethanol, melting at 310°-312° C. with decomposition.

Workup

  1. customAfter completion of the reaction
  2. filtrationa small amount of an isoluble substance is filtered off from the warm mixture
  3. stirringunder stirring at 80°-90° C
  4. filtrationThe precipitated crystals are collected by filtration under reduced pressure
  5. washwashed with water well
  6. customAfter drying
  7. customrecrystallization from dimethylformamide

Sources & evidence

ORD record
ord-71f7cc767c5c484092739b5ad08c5e99
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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