Lithium Hydroxide → 3-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1253650Notes

Reaction equation

HRID 1253650 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH:10]2[NH:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])=[O:6]>CO.O1CCCC1.O.CC(C)=O>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]([NH:16][CH:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:5]([OH:6])=[O:4])[CH:8]=2)[CH2:12][CH2:11]1)=[O:25]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 595055073-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester

Product 1

HCID 595052323-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acidYield 75%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

LiOH (5 equiv.) was added to a suspension of 3-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester (B-01) (11.75 mmol) in methanol (40 ml), tetrahydrofuran (40 ml) and water (30 ml) and the reaction mixture was stirred at 25° C. overnight. Methanol and THF were distilled off, the aqueous residue was acidified with 1N HCl and the mixture was filtered. The white solid obtained was taken up in a mixture of 350 ml of acetone and 50 ml of methanol and the mixture was stirred for 1 h. After filtration, the white solid was dried in vacuo to obtain 3-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid (E-01). Yield: 75%

Workup

  1. distillationMethanol and THF were distilled off
  2. filtrationthe mixture was filtered
  3. customThe white solid obtained
  4. stirringthe mixture was stirred for 1 h
  5. filtrationAfter filtration
  6. customthe white solid was dried in vacuo

Sources & evidence

ORD record
ord-8c5b3badc7684450b6e4f5136b80cfe5
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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