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

HRID 1724766Notes

Reaction equation

HRID 1724766 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 AcidYield 68.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 0.947 mmol) was added to a stirring, room temperature solution of 57 (0.0489 g, 0.1893 mmol) in MeOH (0.47 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (8 min): The reaction was concentrated, redissolved in H20, and extracted with EtOAc (1 mL): 10% aq. HCl was added dropwise to the aqueous layer until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 0.0298 g (68.3%) of 58. 1H (CD3OD, 400 MHz): δ 7.24 (2H, t, J=7.3 Hz), 7.18 (2H, d, J=7.3 Hz), 7.14 (1H, t, J=7.3 Hz), 6.42 (1H, s), 3.11-3.01 (1H, m), 2.95 (1H, dd, J=14.1, 7.3 Hz), 2.89 (1H, dd, J=14.1, 7.8 Hz), 1.26 (3H, d, J=6.8 Hz) ppm. 13C (CD3OD, 100 MHz): δ 164.83, 147.35, 147.13, 143.02, 129.45, 127.92, 127.35, 108.07, 41.46, 35.58, 22.05 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 22.05; CH2 carbons: 35.58; CH carbons: 129.45, 127.92, 127.35, 108.07, 41.46 ppm. HPLC: 8.764 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (8 min)
  4. concentrationThe reaction was concentrated
  5. dissolutionredissolved in H20
  6. extractionextracted with EtOAc (1 mL)
  7. addition10% aq. HCl was added dropwise to the aqueous layer until the pH=2
  8. customThe white solid that precipitated from the reaction
  9. filtrationwas filtered off
  10. washwashed with cold H2O
  11. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-db6a6f5462464f908bdcb0543e97cab6
Source dataset
uspto-grants-2009_02
Patent number
US07488747B2

Reaction notes

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