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

HRID 486183

Reaction equation

HRID 486183 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
82.5 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2e52c32915dd405ea0771bfe9e44394c
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Linked notes

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