Sodium Hydroxide → HCID 21919837, compound

HRID 1768099Notes

Reaction equation

HRID 1768099 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][C:13]([CH3:21])=[N:12]3)[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]([CH3:21])=[N:12]3)[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22280775HCID 22280775, compound

Product 1

HCID 21919837HCID 21919837, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 1-(3-aminobenzisoxazole-5-yl)-3-methyl-5-pyrazole carboxylate (0.14 g) in THF (5 mL) was added NaOH (10% in water, 5 mL). The reaction was stirred at 60° C. for 2 h, THF was evaporated, HCl (10% in water) was added dropwisely until the pH was between 4–5, partitioned between ethylacetate and water, washed with brine, dried over sodium sulfate, filtered and concentrated to give 1-(3-aminobenzisoxazole-5-yl)-3-methyl-5-pyrazole carboxylic acid (0.11 g). ESI mass spectrum z (rel. intensity) 259 (M+H, 100).

Workup

  1. customTHF was evaporated
  2. additionHCl (10% in water) was added dropwisely until the pH
  3. custompartitioned between ethylacetate and water
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9019cc4a1b7c4418bf402549c0b1ea3c
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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