Water → Ammonium Hydroxide

HRID 492337Notes

Reaction equation

HRID 492337 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[K+].[K+].Cl[C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=1.O>CN(C=O)C>[NH4+:19].[OH-:1].[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=2)=[C:3]([CH3:10])[CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 804566-ChloronicotinamideHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 2

HCID 14923Ammonium HydroxideYield 0.7%HCID 597302736-(4-Formyl-2-methyl-phenoxy)-nicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-3-methylbenzaldehyde (1.0 equiv) in DMF (0.2 M solution) was treated with K2CO3 (1.5 equiv) and 6-chloronicotinamide (1.0 equiv). The reaction mixture was placed inside the microwave oven and then irradiated for 5 min. Upon completion of the reaction, the mixture was cooled, poured into H2O and extracted with ethyl acetate, and the combined organic layers were washed twice with water and brine. After drying the extracts over magnesium sulfate and evaporation under vacuum the crude product was purified by silica gel chromatography using CHCl3:EtOH 7%:NH4OH 0.7% to afford the title compound as a solid.

Workup

  1. customirradiated for 5 min
  2. customUpon completion of the reaction
  3. temperaturethe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washthe combined organic layers were washed twice with water and brine
  6. customAfter drying the extracts
  7. customover magnesium sulfate and evaporation under vacuum the crude product
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-425daad17ed9442a876f4914d2f79e39
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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