Sodium Hydroxide → HCID 55285668, compound

HRID 1943954Notes

Reaction equation

HRID 1943954 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[NH:8][N:7]=[C:6]([O:9][CH2:10][CH2:11][OH:12])[C:5]=1C(OCC)=O>C(O)C>[NH2:3][C:4]1[NH:8][N:7]=[C:6]([O:9][CH2:10][CH2:11][OH:12])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178470041HCID 178470041, compound

Product 1

HCID 55285668HCID 55285668, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1M NaOH (46.5 mL, 46.5 mmol) was added to a solution of ethyl 5-amino-3-(2-hydroxyethoxy)-1H-pyrazole-4-carboxylate (2.00 g, 9.29 mmol, prepared as described in Neidlein, Richard, et al. “Heterocyclic Compounds from 2-(Alkoxycarbonylcyanomethylene)-1,3-dioxolanes.” J. Het. Chem. Vol. 26 (1989): pp. 1335-1340) in ethanol (30 mL), and the mixture was refluxed overnight. The solution was washed with DCM with 25% IPA, then acidified to a pH of 3 with concentrated HCl. Gas evolution was observed. The solution was washed with DCM with 25% IPA, and the aqueous layer was evaporated. The residue was treated with methanol, filtered, and the filtrate was evaporated to yield crude 2-(5-amino-1H-pyrazol-3-yloxy)ethanol (3.28 g) along with inorganic salts.

Workup

  1. customprepared
  2. washThe solution was washed with DCM with 25% IPA
  3. washThe solution was washed with DCM with 25% IPA
  4. customthe aqueous layer was evaporated
  5. additionThe residue was treated with methanol
  6. filtrationfiltered
  7. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c491b4219de341db80680775f3bcda06
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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