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

HRID 1681706Notes

Reaction equation

HRID 1681706 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 158%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 (14.63 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-500f5ba07837439fb74a417bc037fdb0
Source dataset
uspto-grants-1992_12
Patent number
US05173493

Reaction notes

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