(4-Isopropyl-phenyl)-(5-methoxy-2-nitro-phenyl)-methanone → (2-Amino-5-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone

HRID 445152Notes

Reaction equation

HRID 445152 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[N+:20]([O-])=O)=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>CO.[Ni]>[NH2:20][C:13]1[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=1[C:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)=[O:11]

Participants

4

Reactant 1

HCID 45140002(4-Isopropyl-phenyl)-(5-methoxy-2-nitro-phenyl)-methanone

Product 1

HCID 45139626(2-Amino-5-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 5.6 g (18.7 mmol) (4-isopropyl-phenyl)-(5-methoxy-2-nitro-phenyl)-methanone in 100 ml methanol is hydrogenated in the presence of 2 g Raney nickel at 5 bar for 5 h. The reaction mixture is filtered and the filtrate is evaporated. The residue is dissolved in ether and the product is precipitated by the addition of gaseous hydrochloric acid as its hydrochloride.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in ether
  4. customthe product is precipitated by the addition of gaseous hydrochloric acid as its hydrochloride

Sources & evidence

ORD record
ord-d122323607074917822bc541d808a9b9
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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