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

HRID 486183ノート

反応式

HRID 486183 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
82.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2e52c32915dd405ea0771bfe9e44394c
出典データセット
uspto-grants-1994_03
特許番号
US05290785

反応ノート

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