Tetrahydrofuran → 6-amino-4-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone

HRID 2209975노트

반응식

HRID 2209975 반응식
O1CCCC1.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([N+:33]([O-])=O)[CH:31]=4)[NH:26][C:25](=[O:36])[CH:24]=3)[CH2:17][CH2:16]2)=[CH:7]1>CO>[NH2:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:36])[CH:24]=[C:23]2[CH2:22][CH2:21][N:18]1[CH2:17][CH2:16][CH:15]([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:6][CH:7]=2)[CH2:20][CH2:19]1

참가 물질

4

반응물 2

HCID 8028TetrahydrofuranHCID 193796784-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-6-nitro-2(1H)-quinolinone

생성물 1

HCID 193796936-amino-4-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-2(1H)-quinolinone수율 77.3%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
55 °C

실험 절차

Into a mixed solvent of tetrahydrofuran (800 ml) and methanol (200 ml) was dissolved 4-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-6-nitro-2(1H)-quinolinone (III-19) (6 g, 14.4 mmol) under heating. Paladium on carbon (2.5 g) was added thereto and the mixture was stirred under hydrogen atmosphere at 55 ° C. for 4 hours. The reaction mixture was filtered at the same temperature and the solvent was distilled off from the filtrate. The residue was dried and then recrystallized from a mixture of methanol, THF and water to give the desired product (III-20) (4.3 g) as pale yellow crystals (mp 214°-216 ° C. (methanol/tetrahydrofuran water)). Yield 77.3 %.

후처리

  1. temperatureunder heating
  2. additionPaladium on carbon (2.5 g) was added
  3. filtrationThe reaction mixture was filtered at the same temperature
  4. distillationthe solvent was distilled off from the filtrate
  5. customThe residue was dried
  6. customrecrystallized from a mixture of methanol, THF and water

출처 및 근거

ORD 기록
ord-ac9aff5d334c4a528ded1df787b81043
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05457099

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