Isopropanol → N4-Phenylquinazoline-4,6-diamine

HRID 411946

Reaction equation

HRID 411946 reaction equation
[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=3)[N:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C)C.O.NN>C(O)C.O.[Ni]>[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=3)[N:11]=[CH:10][N:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 24654Hydrazine hydrate (1:1)HCID 53281896-Nitro-N-phenylquinazolin-4-amine

Product 1

HCID 5328187N4-Phenylquinazoline-4,6-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 4-(phenylamino)-6-nitroquinazoline in ethanol/water and a polar solvent such as iso-propylalcohol is reacted at reflux temperature with hydrazine hydrate and Raney®Nickel. The reaction mixture is filtered, evaporated and purified by silica gel chromatography, to give the product, 4-(phenylamino)-6-aminoquinazoline.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ce5fada03a2a41768303a391ff3f672c
Source dataset
uspto-grants-2003_05
Patent number
US06562319B2

Linked notes

Loading…