Acetic Acid → HCID 13745207, compound

HRID 653136Notes

Reaction equation

HRID 653136 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]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:10][C:9](=[CH:19]O)[C:8]2=O.C(O)(=O)C>CO>[Cl:4][C:5]1[CH:14]=[CH:13][C:12]2[N:11]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:10][C:9]3[CH:19]=[N:3][N:2]([CH3:1])[C:8]=3[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 678721806-Chloro-3-hydroxymethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 13745207HCID 13745207, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylhydrazine(30.56 g) was added dropwise to a mixture of 6-chloro-3-hydroxymethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (160.3 g) and acetic acid(75.8 ml) in methanol (1.6 liters) with stirring and cooling over a period of 10 minutes. After being stirred for 1 hour at room temperature, the mixture was filtered by sunction and the filtrate was evaporated in vacuo after addition of acetic acid (160 ml) to it. The residue was neutralized with aqueous sodium hydroxide under ice cooling. The resulting precipitate was collected by filtration, washed with water and recrystallized from aqueous methanol and then ethanol to give 8-chloro-4,5-dihydro-1-methyl-5-propionyl-1H-pyrazolo[4,3-c]quinoline (65.84 g). The physical data of the compound was identical to that of the object compound of Example 3.

Workup

  1. temperaturecooling over a period of 10 minutes
  2. stirringAfter being stirred for 1 hour at room temperature
  3. filtrationthe mixture was filtered by sunction
  4. customthe filtrate was evaporated in vacuo
  5. additionafter addition of acetic acid (160 ml) to it
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-9cef0e85c0ba40569fcdb2cee00a58f1
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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