HCID 14645053, compound → HCID 14645064, compound

HRID 1032662Notes

Reaction equation

HRID 1032662 reaction equation
[CH3:1][N:2]([CH2:14][CH2:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][CH:18]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1.[H][H]>C(O)C.[Ni]>[NH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][N:2]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([NH2:23])=[O:22])=[CH:24][CH:25]=2)[CH3:1])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 14645053HCID 14645053, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14645064HCID 14645064, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-{2-[N-methyl-N-(4-nitrophenethyl)amino]ethoxy}benzamide (1.4 g) in ethanol (100 ml) was stirred for 16 hours at room temperature under three atmospheres of hydrogen in the presence of Raney nickel ("Nicat 102", Trade Mark). The reaction mixture was filtered and evaporated to dryness to give a yellow solid (1.2 g) which crystallised from ethyl acetate to give the title compound, (1.1 g), m.p. 110°-112°.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-8ed39947311c4ea38ebbf74b25c243eb
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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