(Z)-4-(3-Benzyloxy-4-nitrophenyl)-3-phenyl-but-3-en-2-one → (Z)-4-(4-Amino-3-benzyloxyphenyl)-3-phenyl-but-3-en-2-one

HRID 660488Notes

Reaction equation

HRID 660488 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:18]=[C:19](/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)\[C:20](=[O:22])[CH3:21])[CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pt].CCOC(C)=O>[NH2:15][C:14]1[CH:13]=[CH:12][C:11](/[CH:18]=[C:19](/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)\[C:20](=[O:22])[CH3:21])=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68842235(Z)-4-(3-Benzyloxy-4-nitrophenyl)-3-phenyl-but-3-en-2-one

Product 1

HCID 68839653(Z)-4-(4-Amino-3-benzyloxyphenyl)-3-phenyl-but-3-en-2-one

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (Z) -4-(3-benzyloxy-4-nitrophenyl)-3-phenyl-but-3-en-2-one (760 mg, 2.03 mmol), 5% platinum on carbon (114 mg) in EtOAc (10 mL) is hydrogenated at 1 atm for 18 h. The mixture is filtered through Celite, washed with EtOAc and the filtrate is concentrated. The residue is purified by flash chromatography using methylene chloride/MeOH (100:1) as eluent to give the title compound as a yellow solid.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. washwashed with EtOAc
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-c29bc796fd7547279bacda72e20d6089
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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