4-Hydroxybenzaldehyde → HCID 178497272, compound

HRID 2279106Notes

Reaction equation

HRID 2279106 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[CH3:8][O:9][C:10](=[O:14])[C:11]([CH3:13])=O.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1>C(O)(=O)C.CO>[CH3:8][O:9][C:10]([C:11]1[C:6]2[C:5]([CH3:7])=[N:4][NH:3][C:2]=2[N:1]=[C:20]([C:19]2[CH:22]=[CH:23][C:16]([OH:15])=[CH:17][CH:18]=2)[CH:13]=1)=[O:14]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11748Methyl pyruvateHCID 931461H-Pyrazol-3-amine, 5-methyl-

Product 1

HCID 178497272HCID 178497272, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-amino-5-methylpyrazole (50.0 g), pyruvic acid methyl ester (58.4 g) and 4-hydroxybenzaldehyde (62.9 mL) in acetic acid/methanol (v/v=1/1, 300 mL) was stirred at 75° C. for 15 h, cooled to r.t., and the precipitate formed was isolated by suction filtration and dried in vacuum at 60° C. 6-(4-Hydroxy-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methyl ester (15 g, 10% yield) were obtained as pale yellow solid.

Workup

  1. temperaturecooled to r.t.
  2. customthe precipitate formed
  3. customwas isolated by suction filtration
  4. customdried in vacuum at 60° C

Sources & evidence

ORD record
ord-49ddc5059a8d428e9ffbab9685796403
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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