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

HRID 520437노트

반응식

HRID 520437 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-a44aad467c0b42d4a7b09822216aca3e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326986B2

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