Ethanol → ethyl 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanoate

HRID 1930367Notes

Reaction equation

HRID 1930367 reaction equation
OS(O)(=O)=O.[NH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([CH3:23])([CH3:22])[C:19]([OH:21])=[O:20])[CH:8]=1.C([O-])(O)=O.[Na+].[CH3:29][CH2:30]O>>[NH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([CH3:23])([CH3:22])[C:19]([O:21][CH2:29][CH3:30])=[O:20])[CH:8]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 69034876HCID 69034876, compound

Product 1

HCID 67062996ethyl 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)-2-methylpropanoateYield 91%

Conditions

Temperature
45 °C

Procedure

Cone. H2SO4 (0.5 mL) was added to a solution of 2-(5-amino-1-phenyl-1 H-pyrazol-3-yl)-2-methylpropanoic acid (0.7 g, 28.5 mmol) in EtOH (10 mL) and the reaction was heated at 45° C. for 2 h. The reaction solution was neutralized with aq NaHCO3 and then extracted with EtOAc (3×20 mL). The combined extracts were washed with aq NaHCO3 solution, dried (Na2SO4), and concentrated in vacuo to give ethyl 2-(5-amino-1-phenyl-1 H-pyrazol-3-yl)-2-methylpropanoate (710 mg, 91% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.62 (d, δ 7.6 Hz, 2 H), 7.52 (t, J=7.6 Hz, 2 H), 7.35 (t, J=7.6 Hz, 1 H), 5.47 (s, 1 H), 5.35 (br s, 2 H), 4.12 (q, J= 7.2 Hz, 2 H), 1.50 (s, 6 H), 1.22 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 274.1(M+H+).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined extracts were washed with aq NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8652f33a31f446c588dcf3271aaf2e43
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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