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

HRID 520437Notes

Reaction equation

HRID 520437 reaction equation
[CH3:1][NH2:2].[N+:3]([C:6]1[C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)O[C:15](=[O:16])[C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4]>C1COCC1.CC(O)=O>[CH3:1][N:2]1[C:15](=[O:16])[C:10]2[C:11](=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[CH:8][CH:9]=2)[N:12]=[C:13]1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 585528458-nitro-2-(3-(trifluoromethyl)phenyl)-4H-benzo[d][1,3]oxazin-4-one

Product 1

HCID 585528473-methyl-8-nitro-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-oneYield 89%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methylamine (6.3 mL, 12.5 mmol) in THF was added to a suspension of 8-nitro-2-(3-(trifluoromethyl)phenyl)-4H-benzo[d][1,3]oxazin-4-one 3 (1.5 g, 4.2 mmol) in AcOH (18 mL). The reaction mixture was heated under gentle reflux for 12 h then cooled to room temperature. The volatiles were removed in vacuo and the residue was taken up in EtOAc, washed with sat. aq NaHCO3, brine, dried (MgSO4) and concentrated. The residue was purified by MPLC eluting with pentane/EtOAc (0-75%) to give 4 (1.3 g, 89% yield) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder gentle reflux for 12 h
  3. customThe volatiles were removed in vacuo
  4. washwashed with sat. aq NaHCO3, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC
  8. washeluting with pentane/EtOAc (0-75%)

Sources & evidence

ORD record
ord-a44aad467c0b42d4a7b09822216aca3e
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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