4-Hydroxybenzaldehyde → HCID 178497272, compound

HRID 2360685Notes

Reaction equation

HRID 2360685 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 vacuo at 60° C. 15 g (10%) of the title compound were obtained as pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-62aefe0bcbe74d2db251c5caf70c4997
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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