Sodium Hydroxide → HCID 70655440, compound

HRID 2368037Notes

Reaction equation

HRID 2368037 reaction equation
O[C:2]1([C:10]2[C:11]([NH:16]C(=O)C(C)(C)C)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][CH2:3]1.[OH-].[Na+]>C(O)C>[CH3:8][C:5]1([CH3:9])[CH2:6][CH2:7][C:2]([C:10]2[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:3][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70655407Propanamide, N-[3-(1-hydroxy-4,4-dimethylcyclohexyl)-2-pyridinyl]-2,2-dimethyl-

Product 1

HCID 70655440HCID 70655440, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-(1-hydroxy-4,4-dimethylcyclohexyl)pyridin-2-yl)pivalamide (1.034 g, 3.34 mmol) in ethanol (51 mL) was added 2M aqueous sodium hydroxide solution (16.98 mmol, 8.5 mL). The reaction was heated over night at 100° C. The solvent was evaporated under reduced pressure and the residue was partitionated between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate and the organic layers were combined, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure to yield the title compound as a white solid (706 mg, quant.). MS ISP (m/e): 203.3 (100) [(M+H)+].

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8d5709dbf3da4addb9b766a24e12a310
Source dataset
uspto-grants-2014_04
Patent number
US08703763B2

Reaction notes

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