tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate → Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

HRID 626414Notes

Reaction equation

HRID 626414 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][C:3]=1[N+:17]([O-])=O>[Pd].C(OCC)(=O)C>[NH2:17][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 58136394tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

Product 1

HCID 58136497Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 5.4 g of 10% palladium on carbon were added to a solution of 72.0 g (254 mmol) of tert-butyl (2E)-3-(4-chloro-3-nitrophenyl)acrylate in 1.0 liters of ethyl acetate. The suspension was stirred at RT under a hydrogen atmosphere at standard pressure for 7 h. The reaction mixture was then filtered off with suction through kieselguhr, and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 9:1). This gave 38 g (58% of theory) of the title compound.

Workup

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-d2f2e41eb4034c2d8e3e95067a9310b4
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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