Lithium Hydroxide → 3-(4-chloro-3-oxo-1,2-dihydro-isoindol-2-yl)-2,3-dihydro-1H-indene-5-carboxylic acid
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[N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[Cl:26])[CH2:17]1)=[O:6]>CO.O.CC(C)=O>[Cl:26][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:23]=1[C:24](=[O:25])[N:16]([CH:10]1[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]([OH:6])=[O:4])[CH:8]=3)[CH2:12][CH2:11]1)[CH2:17]2Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
LiOH (5 equiv.) was added to a suspension of 3-(4-chloro-3-oxo-1,2-dihydro-isoindol-2-yl)-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester (D-01) (11.75 mmol) in methanol (90 ml) and water (30 ml) and the reaction mixture was stirred at 25° C. for 72 h. Methanol was 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-(4-chloro-3-oxo-1,2-dihydro-isoindol-2-yl)-2,3-dihydro-1H-indene-5-carboxylic acid (G-01). Yield: 66%
Workup
- distillationMethanol was distilled off
- filtrationthe mixture was filtered
- customThe white solid obtained
- stirringthe mixture was stirred for 1 h
- filtrationAfter filtration
- customthe white solid was dried in vacuo
Sources & evidence
- ORD record
- ord-9837685c48ed4d20bf1f3a7c491b6fb5
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455475B2
Reaction notes
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