Water → N-Methyl-8-nitroquinolin-7-amine

HRID 1615634노트

반응식

HRID 1615634 반응식
[N+:1]([C:4]1[C:5]([NH2:14])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[H-].[Na+].I[CH3:18].O>O1CCCC1>[CH3:18][NH:14][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 129549938-Nitroquinolin-7-amine

생성물 1

HCID 29985233N-Methyl-8-nitroquinolin-7-amine수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 8-nitroquinolin-7-amine (1.89 g, 10 mmol) in tetrahydrofuran (THF) (10 mL) was added sodium hydride (60% wt in mineral oil, 800 mg, 20 mmol). The mixture was stirred at room temperature for 30 minutes, then iodomethane (1.42 g, 10 mmol) was added. The mixture was stirred at room temperature for 5 h. Then water (10 mL) was added. The mixture was extracted with EtOAc, and the organic layer was concentrated. The residue was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 2:1) to give N-methyl-8-nitroquinolin-7-amine as a yellow solid (1.6 g, yield 79%). ESI MS: m/z 204 [M+H]+.

후처리

  1. stirringThe mixture was stirred at room temperature for 5 h
  2. extractionThe mixture was extracted with EtOAc
  3. concentrationthe organic layer was concentrated
  4. customThe residue was purified by silica gel column chromatography (
  5. washeluting with PE/EtOAc v/v 2:1)

출처 및 근거

ORD 기록
ord-449519f78b2b40a3a4bbea6e94e682ee
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765760B2

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