Acetic Acid → HCID 13745205, compound

HRID 653132Notes

Reaction equation

HRID 653132 reaction equation
C[N:2]([CH:4]=[C:5]1[C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:16](=[O:19])[CH2:17][CH3:18])[CH2:6]1)C.O.[NH2:21]N.C(O)(=O)C>CO>[C:16]([N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[NH:21][N:2]=[CH:4][C:5]=2[CH2:6]1)(=[O:19])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 24654Hydrazine hydrate (1:1)HCID 537396133-Dimethylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 13745205HCID 13745205, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-dimethylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.838 g), hydrazine hydrate (0.66 g), and acetic acid (0.792 g) in methanol (30 ml) was stirred at room temperature for 3 hours. To the mixture was added acetic acid (1 ml) and evaporated in vacuo. The residue was dissolved in ethyl acetate, washed successively with aqueous sodium bicarbonate, water, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from ethyl acetate to give 4,5-dihydro-5-propionyl-1H-pyrazolo[4,3-c]quinoline (1.77 g).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed successively with aqueous sodium bicarbonate, water, and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1433c67093cb485a9025ffb3ad1967a3
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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