Glutaric anhydride → 4-[(4-Ethynylphenyl)carbamoyl]butanoic acid

HRID 1039541

Reaction equation

HRID 1039541 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[CH:2].[C:10]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11]1>C(Cl)Cl>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:10](=[O:17])[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1)#[CH:2]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 37600254-Ethynylaniline

Product 1

HCID 248264774-[(4-Ethynylphenyl)carbamoyl]butanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-ethynylaniline (0.99 g, 8.5 mmol) in CH2Cl2 (100 ml) is added glutaric anhydride (1.06 g, 9.30 mmol). After 1 h, the resulting slurry is concentrated by rotary evaporation and the crude mixture is purified by silica column chromatography (10% methanol/5% TEA/CH2Cl2).

Workup

  1. concentrationthe resulting slurry is concentrated by rotary evaporation
  2. customthe crude mixture is purified by silica column chromatography (10% methanol/5% TEA/CH2Cl2)

Sources & evidence

ORD record
ord-9e4878eddd2240059eb2c5c6c7987521
Source dataset
uspto-grants-2013_10
Patent number
US08552173B2

Linked notes

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