tert-Butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropanecarboxylate → tert-Butyl 1-[(3-amino-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate

HRID 1475678Notes

Reaction equation

HRID 1475678 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:19])[C:9]2([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11][CH2:10]2)=[CH:4][C:3]=1[N+:20]([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:20][C:3]1[CH:4]=[C:5]([CH:8]([OH:19])[C:9]2([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:10][CH2:11]2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67958223tert-Butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67957785tert-Butyl 1-[(3-amino-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.72 g (8.30 mmol) of tert-butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropane-carboxylate were dissolved in 100 ml of ethyl acetate, and 177 mg of palladium on carbon (10%) were added. For three days, the reaction mixture was stirred vigorously under a stationary atmosphere of hydrogen at atmospheric pressure. The mixture was then filtered through Celite and the filtrate obtained was evaporated to dryness. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 1.97 g of the target compound (80% of theory).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. customthe filtrate obtained
  3. customwas evaporated to dryness
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-995c9272c1e84bc7bea44c1951a2c89f
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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