Water → 4-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 1878031Notes

Reaction equation

HRID 1878031 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:7](=[O:21])[NH:6][C:5]2([CH2:26][N+:27]([O-])=O)[C:22]([F:25])([F:24])[F:23].[Cl-].[NH4+].O>CO.[Fe]>[NH2:27][CH2:26][C:5]1([C:22]([F:24])([F:25])[F:23])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[N:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:7](=[O:21])[NH:6]1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 684911796-Bromo-1-(4-methoxybenzyl)-4-(nitromethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 684886144-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent2×

Procedure

6-Bromo-1-(4-methoxybenzyl)-4-(nitromethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (1.0 g, 2.1 mmol), iron (294 mg, 5.3 mmol) and ammonium chloride (562 mg, 10.5 mmol) were stirred in methanol (5 mL) and water (5 mL) and the resulting solution was heated overnight under reflux. After the reaction solution was cooled to room temperature, methanol (10 mL) was added thereto, and the mixture was stirred at room temperature for 1 hour. After the resulting solid was removed by filtration, the mother liquid was concentrated, and the residue was washed sequentially with water and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure, whereby the objective compound (958 mg, quant.) was obtained as a colorless foamy solid.

Workup

  1. temperatureunder reflux
  2. customAfter the resulting solid was removed by filtration
  3. concentrationthe mother liquid was concentrated
  4. washthe residue was washed sequentially with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter the drying agent was removed by filtration
  7. customthe solvent was evaporated under reduced pressure, whereby the objective compound (958 mg, quant.)
  8. customwas obtained as a colorless foamy solid

Sources & evidence

ORD record
ord-dee237c2464647dfb08703c87693d45e
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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