Sodium Hydroxide → 5-(2-phenylpropyl)-1H-pyrazole-3-carboxylic Acid

HRID 1434769Notes

Reaction equation

HRID 1434769 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[NH:10][N:9]=1)=[O:7])C>CO>[C:16]1([CH:14]([CH3:15])[CH2:13][C:11]2[NH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57435096HCID 57435096, compound

Product 1

HCID 118454695-(2-phenylpropyl)-1H-pyrazole-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 1.01 mmol) was added to a stirring, room temperature solution of 61 (0.0523 g, 0.2024 mmol) in MeOH (0.51 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (9 min): The reaction was concentrated, redissolved in H2O, and extracted with EtOAc. 10% aq. HCl was added dropwise to the aqueous layer until the pH=2. When a white solid did not precipitate as expected, EtOAc was added, and the organic layer was removed, dried with Na2SO4, filtered, and concentrated to provide pure 62. 1H (CD3OD, 400 MHz): δ 7.24-7.18 (2H, m), 7.17-7.05 (3H, m), 6.56 (1H, s), 3.17 (1H, app sex, J=7.3 Hz), 2.96 (1H, dd, J=13.6, 7.3 Hz), 2.80 (1H, dd, J=13.7, 7.8 Hz), 1.25 (3H, d, J=6.8 Hz) ppm. 13C (CD3OD, 100 MHz): 6164.88, 153.40, 142.91, 140.97, 130.09, 129.25, 127.21, 106.11, 44.41, 34.96, 20.35 ppm. DEPT (CD3OD, 100 MHz): CH3 carbon: 20.35; CH2 carbon: 44.41; CH carbons: 130.09, 129.25, 127.21, 106.11, 34.96 ppm. HPLC: 8.849 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (9 min)
  4. concentrationThe reaction was concentrated
  5. dissolutionredissolved in H2O
  6. extractionextracted with EtOAc
  7. addition10% aq. HCl was added dropwise to the aqueous layer until the pH=2
  8. customWhen a white solid did not precipitate
  9. additionEtOAc was added
  10. customthe organic layer was removed
  11. dry with materialdried with Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto provide pure 62
  15. custom8.849 min.

Sources & evidence

ORD record
ord-aeb0e4d023a8485f89df12819df25f64
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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