Cyclohexane ethylacetate → Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

HRID 877219Notes

Reaction equation

HRID 877219 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.C1CCCCC1.C(OCC)(=O)C>[Pd].C(O)C.C1COCC1>[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

6

Reactant 2

HCID 21867204Cyclohexane ethylacetateHCID 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 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, 500 mg of palladium on carbon (10%) were added to a solution of 6.74 g (23.76 mmol) of tert-butyl(2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate in 200 ml of ethanol and 20 ml of THF, and the mixture was hydrogenated under atmospheric pressure for 12 hours. After the reaction had gone to completion (monitored by TLC; mobile phase cyclohexane/ethyl acetate 1:1), the reaction solution was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1). This gave 1.40 g (5.47 mmol, 23% of theory) of the title compound.

Workup

  1. filtrationthe reaction solution was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1)

Sources & evidence

ORD record
ord-7d6d03eaa0544af1bc3b5bb2f6562a64
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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