4-(5-Nitro-thiophen-2-yl)-butyric acid methyl ester → 4-(5-Amino-thiophen-2-yl)-butyric acid methyl ester

HRID 1178618Notes

Reaction equation

HRID 1178618 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([N+:12]([O-])=O)=[CH:10][CH:11]=1>C(OCC)(=O)C.CO.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([NH2:12])=[CH:10][CH:11]=1

Participants

5

Reactant 1

HCID 692334004-(5-Nitro-thiophen-2-yl)-butyric acid methyl ester

Product 1

HCID 692355624-(5-Amino-thiophen-2-yl)-butyric acid methyl esterYield 66.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(5-nitro-thiophen-2-yl)-butyric acid methyl ester (2.29 g, 10.0 mmol) and palladium hydroxide (500 mg, 20% on carbon) in 30 mL of ethyl acetate and 30 mL of methanol is hydrogenated at 50 psi for 48 hours. The reaction mixture is filtered and concentrated. The residue is purified by flash column chromatography eluting with 1:3 ethyl acetate:hexane to provide 1.32 g of 4-(5-amino-thiophen-2-yl)-butyric acid methyl ester as a dark oil; 1H NMR (DMSO-d6) δ 1.74 (m, 2H), 2.38 (m, 2H), 2.54 (m, 2H), 3.59 (s, 3H), 5.66 (d, J=3 Hz, 1H), 6.24 (d, J=3 Hz, 1H); MS 200.2 (M+H)+.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated
  3. customThe residue is purified by flash column chromatography
  4. washeluting with 1:3 ethyl acetate

Sources & evidence

ORD record
ord-6fb2f4ca49e4411f80b45c1c82380c6a
Source dataset
uspto-grants-2007_10
Patent number
US07276519B2

Reaction notes

Loading…