Sodium Hydroxide → 2-(4-Carboxybenzamido)-4-isobutyramidobenzoic acid
Reaction equation
[C:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])=[O:9])=[CH:6][CH:5]=1)([OH:3])=[O:2].[C:23](Cl)(=[O:27])[CH:24]([CH3:26])[CH3:25].[OH-].[Na+]>N1C=CC=CC=1.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([NH:20][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])=[O:9])=[CH:21][CH:22]=1)([OH:3])=[O:2]Participants
6
Procedure
A solution of 1.5 g of 2-(4-carboxybenzamido)-4-aminobenzoic acid in 50 ml of pyridine was mixed with 3.2 g of isobutyroyl chloride and the mixture was heated at 50° to 60° C. for a period of 2 hours. The reaction mixture was further mixed with a solution of 4 g of sodium hydroxide in 20 ml of water and concentrated under vacuum. The residue was diluted with water and hydrochloric acid was used to adjust the pH of the dilution between 1 and 2. The precipitating crystal was filtered, washed with water and recrystallized from a solvent mixture of methanol and water to thereby produce 1.1 g of 2-(4-carboxybenzamido)-4-isobutyramidobenzoic acid having a melting point in the range of from 312° to 314° C. (decompose).
Workup
- temperaturethe mixture was heated at 50° to 60° C. for a period of 2 hours
- concentrationconcentrated under vacuum
- additionThe residue was diluted with water and hydrochloric acid
- filtrationThe precipitating crystal was filtered
- washwashed with water
- customrecrystallized from a solvent mixture of methanol and water
Sources & evidence
- ORD record
- ord-2d29ce57b2eb4928bc1794f9d5e880fc
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04221814
Reaction notes
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