4-Hydroxybenzaldehyde → HCID 178497271, compound

HRID 2279161Notes

Reaction equation

HRID 2279161 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH:7]2[CH2:9][CH2:8]2)[NH:4][N:3]=1.[CH3:10][O:11][C:12](=[O:16])[C:13]([CH3:15])=O.[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1>C(O)(=O)C.CO>[CH3:10][O:11][C:12]([C:13]1[C:6]2[C:5]([CH:7]3[CH2:9][CH2:8]3)=[N:4][NH:3][C:2]=2[N:1]=[C:22]([C:21]2[CH:24]=[CH:25][C:18]([OH:17])=[CH:19][CH:20]=2)[CH:15]=1)=[O:16]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11748Methyl pyruvateHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 178497271HCID 178497271, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-amino-5-cyclopropylpyrazole (8.95 g), pyruvic acid methyl ester (8.24 g) and 4-hydroxybenzaldehyde (8.87 g) in acetic acid/methanol (v/v=1/1, 120 mL) was stirred at 75° C. for 14 h. The methanol was removed in vacuo, and the remaining mixture was poured unto water, and extracted with ethyl acetate three times. The combined organic phases were washed with brine, dried over magnesium sulfate, filtrated and concentrated in vacuo. The residue was dissolved in 50 ml of acetic acid/methanol (v/v=1/1), heated to reflux for 1 h and cooled to r.t. The precipitated product was isolated by filtration and dried in vacuo at 60° C. 3.80 g (17%) of the title compound were obtained.

Workup

  1. customThe methanol was removed in vacuo
  2. additionthe remaining mixture was poured unto water
  3. extractionextracted with ethyl acetate three times
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in 50 ml of acetic acid/methanol (v/v=1/1)
  9. temperatureheated
  10. temperatureto reflux for 1 h
  11. temperaturecooled to r.t
  12. customThe precipitated product was isolated by filtration
  13. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-ea78ab0d06fb48da8accc9f531a56319
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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