4-Quinazolinamine, N,2-dimethyl-N-(4-nitrophenyl)- → N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine

HRID 1436286Notes

Reaction equation

HRID 1436286 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>C(OCC)(=O)C.[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([CH3:1])[N:11]=2)[CH3:13])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 111505524-Quinazolinamine, N,2-dimethyl-N-(4-nitrophenyl)-

Product 1

HCID 11311597N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamineYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-methyl-quinazolin-4-yl)-(4-nitro-phenyl)-methylamine (200 mg, 0.68 mmol) in 25 mL of ethyl acetate was hydrogenated over Palladium on carbon (70 mg) at 50 psi for 4 h, and the reaction mixture was filtered through a pad of celite and concentrated. The resulting crude product was purified by chromatography (50% ethyl acetate/hexane) to obtain the title compound (140 mg, 78%). 1H NMR (CDCl3): 7.71 (m, 1H), 7.51 (ddd, J=8.4, 6.9, 1.5, 1H), 7.09 (m, 1H), 6.93-7.05 (m, 3H), 6.68 (m, 2H), 3.74 (s, broad, 2H), 3.56 (s, 3H), 2.71 (s, 3H).

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated
  3. customThe resulting crude product was purified by chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-42c4742d0da5469f83a56554878c2181
Source dataset
uspto-grants-2009_11
Patent number
US07618975B2

Reaction notes

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