4-[4-(2-Nitro-phenyl)-oxazol-2-yl]-butyric acid methyl ester → 4-[4-(2-Amino-phenyl)-oxazol-2-yl]-butyric acid methyl ester

HRID 1616622Notes

Reaction equation

HRID 1616622 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][C:7]1[O:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[N:11]=1.[H][H]>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][C:7]1[O:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[N:11]=1

Participants

5

Reactant 2

HCID 591677914-[4-(2-Nitro-phenyl)-oxazol-2-yl]-butyric acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 591677464-[4-(2-Amino-phenyl)-oxazol-2-yl]-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

Combine 4-[4-(2-nitro-phenyl)-oxazol-2-yl]-butyric acid methyl ester (3.0 g, 10.3 mmol) with Pd/C (5%, 450 mg) and Pd/black (50 mg) in THF (150 mL) and react with hydrogen (init. 40 psi) in a Parr® apparatus. When reduction is complete, filter the mixture through Celite® and concentrate the filtrate. Drying allows for recovery of crude 4-[4-(2-amino-phenyl)-oxazol-2-yl]-butyric acid methyl ester (2.36 g, 88%). MS (ES): (M+1)+ 261.2 m/z.

Workup

  1. filtrationfilter the mixture through Celite®
  2. concentrationconcentrate the filtrate
  3. customDrying

Sources & evidence

ORD record
ord-5b5f9ac594e94a28b997653186ac8992
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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