Formamide → 8-Nitroquinazolin-4-ol

HRID 513741

반응식

HRID 513741 반응식
[CH:1]([NH2:3])=O.[NH2:4][C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8]>COC(O)C>[N+:14]([C:13]1[CH:12]=[CH:11][CH:10]=[C:6]2[C:5]=1[N:4]=[CH:1][NH:3][C:7]2=[O:8])([O-:16])=[O:15]

참가 물질

4

반응물 2

HCID 713FormamideHCID 2196332-Amino-3-nitrobenzoic acid

생성물 1

HCID 1354087998-Nitroquinazolin-4-ol수율 14.3%

시약·촉매·용매 1

HCID 30156371-Methoxyethanol용매

실험 절차

Formamide (17.1 g, 380 mmol) was added to a solution of 2-amino-3-nitrobenzoic acid (2.0 g, 11 mmol) in methoxy ethanol (5 ml) and the reaction was heated at 200 C in a sealed tube for 17 h. After cooling, the mixture was concentrated in vacuo. The residue was quenched with sat. aq. NaHCO3 solution and the aqueous phase was extracted with EtOAc (100 ml, ×2). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (300 mg, 14%).

후처리

  1. temperaturethe reaction was heated at 200 C in a sealed tube for 17 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was quenched with sat. aq. NaHCO3 solution
  5. extractionthe aqueous phase was extracted with EtOAc (100 ml, ×2)
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by column chromatography with DCM as the eluent

출처 및 근거

ORD 기록
ord-67fde05214b644d69083949debd3385c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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