Ethanol → HCID 67063086, compound

HRID 1930369Notes

Reaction equation

HRID 1930369 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH:3]=1.OS(O)(=O)=O.C([O-])(O)=[O:19].[Na+].[CH3:23][CH2:24][OH:25]>>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([CH3:12])([CH3:11])[C:9]([O:25][CH2:24][CH3:23])=[O:19])[CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 69038672HCID 69038672, compound

Product 1

HCID 67063086HCID 67063086, compoundYield 44%

Procedure

A mixture of 2-(5-amino-1-methyl-1 H-pyrazol-3-yl)-2-methylpropanenitrile (1.4 g, 8.5 mmol) in EtOH (30 mL) was treated with cone. H2SO4 (3 mL) and the resulting mixture was refluxed for 10 days. The reaction mixture was neutralized with saturated aq NaHCO3 solution, and the mixture was extracted with EtOAc. The organics were washed with brine, dried (MgSO4) and concentrated in vacuo. Recrystallization (EtOAc/petroleum ether) provided ethyl 2-(5-amino-1-methyl-1 H-pyrazol-3-yl)-2-methylpropanoate (0.8 g, 44% yield). 1H NMR (300 MHz, DMSO-d6): δ5.13 (s, 1 H), 5.04 (s, 2 H), 4.00 (q, J=6.9 Hz, 2 H), 3.41 (s, 3 H), 1.11 (t, J=6.9 Hz, 6 H); MS (ESI) m/z: 212.0 [M+H]+.

Workup

  1. additionwas treated with cone
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customRecrystallization (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-8d8e43756bf248e9bbfbf2e308574e22
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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