HCID 24757386, compound → HCID 24757470, compound

HRID 1640008Notes

Reaction equation

HRID 1640008 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([CH3:26])[C:19]([O:21]C(C)(C)C)=[O:20])=[CH:14][CH:13]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1>C(O)=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:12]3[CH:13]=[CH:14][C:15]([CH:18]([CH3:26])[C:19]([OH:21])=[O:20])=[CH:16][CH:17]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 24757386HCID 24757386, compound

Product 1

HCID 24757470HCID 24757470, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of tert-butyl 2-(4-(6-chloro-1-oxoisoindolin-2-yl)phenyl)propanoate (0.157 g, 0.422 mmol) and formic acid (15.7 mL) was stirred overnight at room temperature. The mixture was then concentrated under reduced pressure, suspended in hexanes (5 mL), sonicated, and the solids collected by filtration to afford 2-(4-(6-chloro-1-oxoisoindolin-2-yl)phenyl)propanoic acid (0.118 g, 89%) as a white solid: mp 235-248° C. (dec); 1H NMR (500 MHz, DMSO-d6) δ 12.35 (br s, 1H), 7.83 (d, J=8.5 Hz, 2H), 8.44 (s, 1H), 7.78 (m, 2H), 7.51 (m, 2H), 5.02 (s, 2H), 3.69 (q, J=7.0 Hz, 1H), 1.38 (d, J=7.0 Hz, 3H); ESI MS m/z 348 [M+H+CH3OH]+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customsonicated
  3. filtrationthe solids collected by filtration

Sources & evidence

ORD record
ord-13735fba7230434e9ab45e4ff7e22708
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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