Ethyl benzoylacetate → HCID 178433989, compound

HRID 1764094Notes

Reaction equation

HRID 1764094 reaction equation
C(O[C:4](=[O:14])[CH2:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[NH2:15][C:16]1[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[CH:17]=1>O>[CH3:21][N:20]1[C:16]2=[N:15][C:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:5][C:4]([OH:14])=[C:17]2[C:18]([CH3:22])=[N:19]1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Product 1

HCID 178433989HCID 178433989, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

96 gms. of benzoylacetic acid ethyl ester (0.5 mol.) are added dropwise to a stirred mixture of 55.5 gms. of 5-amino-1,3-dimethylpyrazole (0.5 mol) and 250 gms. of polyphosphorus acid heated to 120° C. After the reaction has occurred, which can be recognized by the changing of the color, the whole is heated for an additional hour at 120° C. After the mixture has cooled to room temperature, 600 ml. of water are added and stirring is continued until the compound becomes crystalline. The mixture is allowed to stand overnight and is then filtered off. The collected 1,3-dimethyl-4-hydroxy-6-phenyl-1H-pyrazolo[3,4-b]pyridine is washed with dilute ammonia, dried and treated with ethyl acetate yielding 73.6 gms. (61.6%), m.p. 262°-264°.

Workup

  1. temperaturethe whole is heated for an additional hour at 120° C
  2. temperatureAfter the mixture has cooled to room temperature
  3. filtrationis then filtered off
  4. washThe collected 1,3-dimethyl-4-hydroxy-6-phenyl-1H-pyrazolo[3,4-b]pyridine is washed with dilute ammonia
  5. customdried
  6. additiontreated with ethyl acetate yielding 73.6 gms

Sources & evidence

ORD record
ord-7a008de488e842b6b3c7d19438a84541
Source dataset
uspto-grants-1978_09
Patent number
US04115394

Reaction notes

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