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

HRID 520437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520437
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-a44aad467c0b42d4a7b09822216aca3e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326986B2

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