3-methyl-8-nitro-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one → 8-amino-3-methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one

HRID 520438

Reaction equation

HRID 520438 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([N+:13]([O-])=O)[CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1>C1COCC1.[Pd]>[NH2:13][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[N:2]([CH3:1])[C:11]2=[O:12]

Participants

4

Reactant 1

HCID 585528473-methyl-8-nitro-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one

Product 1

HCID 585528228-amino-3-methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-oneYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C 10 wt % (100 mg) was added to a degassed solution of 3-methyl-8-nitro-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one 4 (1.3 g, 3.7 mmol) in THF (35 mL). The mixture was hydrogenated under balloon pressure for 12 h. The catalyst was removed by filtration and the solvent evaporated. The residue was purified by MPLC eluting with pentane/EtOAc (0-50%) to give 5 (1.1 g, 90% yield) as a yellow solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. customThe residue was purified by MPLC
  4. washeluting with pentane/EtOAc (0-50%)

Sources & evidence

ORD record
ord-c7c3d3f51a474447b0c08cb58f1ddbdf
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Linked notes

Loading…