Methyl 3-(4-nitrophenyl)-2-propenoate → Methyl 3-(4-aminophenyl)propanoate

HRID 386436

Reaction equation

HRID 386436 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1)([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 5354137Methyl 3-(4-nitrophenyl)-2-propenoate

Product 1

HCID 417374Methyl 3-(4-aminophenyl)propanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methyl (E)-3-(4-nitrophenyl)acrylate (S31, 4.10 g, 19.8 mmol) in MeOH (30 mL) and THF (30 mL) was treated with 10% Pd/C (400 mg). The reaction mixture was purged with H2 and was stirred at 25° C. for 10 h. The suspension was filtered through diatomaceous earth and concentrated to afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid: 1H NMR (CDCl3, 500 MHz) 6.99 (d, 2H, J=8.2 Hz), 6.63 (d, 2H, J=8.4 Hz), 3.60 (s, 3H), 2.85 (t, 2H, J=7.7 Hz), 2.58 (t, 2H, J=7.7 Hz); 13C NMR (CDCl3, 125 MHz) 173.5, 144.6, 130.5, 129.1, 115.3, 51.5, 36.1, 30.1.

Workup

  1. customThe reaction mixture was purged with H2
  2. filtrationThe suspension was filtered through diatomaceous earth
  3. concentrationconcentrated
  4. customto afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid

Sources & evidence

ORD record
ord-77a0dd304c9441dd91cb47a29775c16c
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Linked notes

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