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Water → 2-(2-Bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047888
Notes
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Reaction equation

HRID 1047888 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[Br:24])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[Br:24][C:18]1[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593141512-(2-Bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593141842-(2-Bromo-4-methyl-benzoylamino)-indan-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (445 mg, 1.11 mmol) is dissolved in EtOH (15 mL), and solid KOH (1.42 g, 24.7 mmol) and water (1.5 mL) are added. The mixture is stirred at RT for 30 min then concentrated in vacuo. The residue is dissolved in water (10 mL) and acidified with conc. HCl until no more white solid precipitated. The solid is collected by vacuum filtration to give product (277) as white solid (415 mg, 100%).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue is dissolved in water (10 mL)
  3. customprecipitated
  4. filtrationThe solid is collected by vacuum filtration

Sources & evidence

ORD record
ord-86a12fc8670d43b685569df0377632ed
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569535B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes