Ethanol → HCID 44769651, compound

HRID 1690143Notes

Reaction equation

HRID 1690143 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[H-].[Na+].[CH2:14]([OH:16])[CH3:15]>>[CH2:14]([O:16][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][N:3]=1)[CH3:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 123642306-Chloro-N-methylnicotinamide

Product 1

HCID 44769651HCID 44769651, compoundYield 100%

Procedure

To a solution of 6-chloro-N-methylnicotinamide (500 mg, 2.93 mmol) in ethanol (10 mL), sodium hydride (purity 50%) (176 mg, 7.33 mmol) was added under ice-cold conditions. The resultant mixture was heated to reflux for 8 hours. After completion of the reaction, the reaction solution was concentrated in vacuo, then filtered, washed with water and ethyl acetate, and then dried. 6-Ethoxy-N-methylnicotinamide (556 mg, yield >100%) was obtained as a white crystal.

Workup

  1. temperatureto reflux for 8 hours
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated in vacuo
  4. filtrationfiltered
  5. washwashed with water and ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-81fb366158cc432e953e478adc6dace6
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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