HCID 71272686, compound → 5-Amino-1H-pyrazole-3-ethanol

HRID 475073Notes

Reaction equation

HRID 475073 reaction equation
COC1C=CC(C[O:8][CH2:9][CH2:10][C:11]2[NH:15][N:14]=[C:13]([NH2:16])[CH:12]=2)=CC=1>C(O)(C(F)(F)F)=O>[NH2:16][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][OH:8])[NH:15][N:14]=1

Participants

3

Reactant 1

HCID 71272686HCID 71272686, compound

Product 1

HCID 697622065-Amino-1H-pyrazole-3-ethanolYield 38%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution 5-(2-((4-methoxy-benzyl)oxy)-ethyl)-1H-pyrazol-3-amine (66 g, 334.4 mmol) in TFA (300 mL) was heated under reflux for 16 h. After being cooled to RT, the solvent was removed in vacuo, and the residue was partitioned between DCM (400 mL) and 2 N aqueous NaHCO3 (200 mL). The organic layer was separated and the aqueous layer was extracted with DCM (3×100 mL). The combined organic layers were washed with brine, dried (Na2SO4) and then concentrated in vacuo to afford 13 g (38%) of 2-(3-amino-1H-pyrazol-5-yl)ethanol as a yellow solid.

Workup

  1. temperatureunder reflux for 16 h
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between DCM (400 mL) and 2 N aqueous NaHCO3 (200 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with DCM (3×100 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56d9a9fa4bbe47238479798f3f905d28
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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