Acetic Acid → Quinoline

HRID 653137Notes

Reaction equation

HRID 653137 reaction equation
CNN.Cl[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11](C=O)[CH2:10][C:9](=CO)[C:8]2=O.C(O)(=O)C>CO>[N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=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 7047QuinolineYield 116%

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-e613a3734bee4f00b4d2bbfa9dc02cc2
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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