Acetic Acid → 8-chloro-4,5-dihydro-5-formyl-1-methyl-1H-pyrazolo[4,3-c]quinoline

HRID 35687Notes

Reaction equation

HRID 35687 reaction equation
[CH3:1][NH:2][NH2:3].[Cl:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]=[O:16])[CH2:10][C:9](=[CH:17]O)[C:8]2=O.C(O)(=O)C>CO>[Cl:4][C:5]1[CH:14]=[CH:13][C:12]2[N:11]([CH:15]=[O:16])[CH2:10][C:9]3[CH:17]=[N:3][N:2]([CH3:1])[C:8]=3[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 737627696-Chloro-1-formyl-3-hydroxymethylene-4-oxo-1,2,3,4-tetrahydroquinoline

Product 1

HCID 212948228-chloro-4,5-dihydro-5-formyl-1-methyl-1H-pyrazolo[4,3-c]quinolineYield 61.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylhydrazine (52.5 g) was dropwise to a mixture of 6-chloro-1-formyl-3-hydroxymethylene-4-oxo-1,2,3,4-tetrahydroquinoline (276 g) and acetic acid (13 ml) in methanol (2.76 liters) at 10° C. to 12° C. over a period of 10 minutes. After being stirred for 1.5 hours at the same temperature, the resulting precipitate was collected by filtration, washed with methanol and dried to give 8-chloro-4,5-dihydro-5-formyl-1-methyl-1H -pyrazolo[4,3-c]quinoline (174 g).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with methanol
  3. customdried

Sources & evidence

ORD record
ord-1c3f8009f6f24e4a9b0e938a341db64b
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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