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

HRID 19459

Reaction equation

HRID 19459 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[CH:17])=[CH:12][CH:11]=1>ClCCl>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:5]([CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])=[O:6])=[CH:11][CH:12]=1)#[CH:17]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 37600254-Ethynylaniline

Product 1

HCID 248264774-[(4-Ethynylphenyl)carbamoyl]butanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Glutaric anhydride (540 mg, 4.70 mmol) was dissolved in anhydrous dichloromethane (7 mL) and followed with the addition of p-aminophenyl-acetylene (500 mg, 4.27 mmol). The mixture was allowed to stir at room temperature for 6 hours before the solvent was evaporated under reduced pressure to provide 900 mg of a yellow white product 24 (96%); mp 135-140° C.; 1H NMR (DMSO-d6, 300 MHz) δ 1.77 (p, J=8.21 Hz, 2H), 2.25 (t, J=9.30 Hz, 2H), 2.34 (t, J=6.56 Hz, 2H), 4.05 (s, 1H), 7.38 (d, J=8.52 Hz, 2H), 7.59 (d, J=7.91 Hz, 2H) 9.90 (s, 1H); HRMS m/e calculated for (M+H)+: C13H13NO3 231.0895; found 231.0895.

Workup

  1. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-ff5b7f31a9314cb5b8450f6baebb601a
Source dataset
uspto-grants-2010_06
Patent number
US07745229B2

Linked notes

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