Potassium Hydroxide → HCID 66687759, compound

HRID 1625295Notes

Reaction equation

HRID 1625295 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[O:17][C:18]3[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=3[C:20]=2[CH2:21][N:22]([CH3:24])[CH3:23])=[O:15])=[CH:6][CH:5]=1.[OH-].[K+:31]>CO>[K+:31].[CH3:24][N:22]([CH2:21][C:20]1[C:19]2[CH:25]=[CH:26][CH:27]=[CH:28][C:18]=2[O:17][C:16]=1[C:14]([NH:13][CH2:12][CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([O-:29])=[O:2])=[CH:9][CH:8]=1)=[O:15])[CH3:23]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59582127HCID 59582127, compound

Product 1

HCID 66687759HCID 66687759, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4-{2-[(3-Dimethylaminomethylbenzofuran-2-carbonyl)amino]ethoxy}benzoic acid methyl ester (70.0 g, 0.177 mol) was suspended in methanol (350 ml). 50% Potassium hydroxide (139.8 g, 1.062 mol) was added and the reaction mixture was heated to 60° C. until completion of reaction. After cooling to room temperature, the resulting crystals were filtered on a coarse frit and washed with methanol. The crystals were dried in vacuo to give 4-{2-[(3-dimethylaminomethylbenzofuran-2-carbonyl)amino]ethoxy}benzoic acid potassium salt (72.0 g) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting crystals were filtered on a coarse frit
  3. washwashed with methanol
  4. customThe crystals were dried in vacuo

Sources & evidence

ORD record
ord-26ba7418ee5f477bb5b9ee6bd04030f0
Source dataset
uspto-grants-2014_07
Patent number
US08779171B2

Reaction notes

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