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

HRID 520437ノート

反応式

HRID 520437 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-a44aad467c0b42d4a7b09822216aca3e
出典データセット
uspto-grants-2016_05
特許番号
US09326986B2

反応ノート

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