Sulfuric Acid → 2-chloro-8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one

HRID 486183

반응식

HRID 486183 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[CH3:11][CH:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]1=O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[N:9]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]1=[C:12]2[CH3:11]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 709452-Methyl-1,3-cyclohexanedioneHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

생성물 1

HCID 103539602-chloro-8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one수율 50%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
82.5 °C

실험 절차

To a suspension of p-chlorophenylhydrazine hydrochloride (8.52 g) in toluene (100 ml) were added 2-methylcyclohexane-1,3-dione (5.0 g) and 40% sulfuric acid (40 ml), and the mixture was stirred at 80-85° C. for 4 hours. After cooling, the organic layer was separated. The aqueous layer was extracted with toluene. The organic layers were combined and washed with aqueous sodium bicarbonate, water, and brine. After dried over sodium sulfate, the organic layer was evaporated. The residue was recrystallized from methanol to give 2-chloro-8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one (4.63 g).

후처리

  1. temperatureAfter cooling
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with toluene
  4. washwashed with aqueous sodium bicarbonate, water, and brine
  5. dry with materialAfter dried over sodium sulfate
  6. customthe organic layer was evaporated
  7. customThe residue was recrystallized from methanol

출처 및 근거

ORD 기록
ord-2e52c32915dd405ea0771bfe9e44394c
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290785

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