Acetic Acid → 4,5-dihydro-8-nitro-5-propionyl-1H-pyrazolo[4,3-c]quinoline

HRID 653131Notes

Reaction equation

HRID 653131 reaction equation
C(Cl)(Cl)Cl.C[N:6]([CH:8]=[C:9]1[C:18](=O)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=2)[N:11]([C:23](=[O:26])[CH2:24][CH3:25])[CH2:10]1)C.O.[NH2:28]N.C(O)(=O)C>CO>[N+:20]([C:15]1[CH:14]=[CH:13][C:12]2[N:11]([C:23](=[O:26])[CH2:24][CH3:25])[CH2:10][C:9]3[CH:8]=[N:6][NH:28][C:18]=3[C:17]=2[CH:16]=1)([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 6212ChloroformHCID 24654Hydrazine hydrate (1:1)HCID 54552519HCID 54552519, compound

Product 1

HCID 137452084,5-dihydro-8-nitro-5-propionyl-1H-pyrazolo[4,3-c]quinolineYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Chloroform (50 ml) was added to a mixture of 3-dimethylaminomethylene-6-nitro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (3.03 g), hydrazine hydrate (0.6 g), and acetic acid (0.78 g) in methanol (50 ml) and stirred at room temperature for 8 hours. To the mixture was added acetic acid (2 ml) and evaporated in vacuo. The residual solid was washed with water, dried, and recrystallized from a mixture of chloroform and methanol to give 4,5-dihydro-8-nitro-5-propionyl-1H-pyrazolo[4,3-c]quinoline (2.53 g).

Workup

  1. customevaporated in vacuo
  2. washThe residual solid was washed with water
  3. customdried
  4. customrecrystallized from a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-c4f53a4cec824ad89734de24f6fbe62d
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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