2-Methoxybenzaldehyde → HCID 59553893, compound

HRID 1170919Notes

Reaction equation

HRID 1170919 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9])=[C:6]([Cl:19])[N:5]=[CH:4][CH:3]=1.[CH:20](=O)[C:21]1[C:22]([O:27][CH3:28])=[CH:23][CH:24]=[CH:25][CH:26]=1>C(#N)C.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:19][C:6]1[C:7]2[C:8](=[O:9])[N:10]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])[NH:1][C:2]=2[CH:3]=[CH:4][N:5]=1

Participants

6

Reactant 2

HCID 86582-MethoxybenzaldehydeHCID 59553897HCID 59553897, compound

Product 1

HCID 59553893HCID 59553893, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-amino-2-chloro-N-phenethyl-nicotinamide (808 mg, 2.93 mmol) in 8 mL of acetonitrile at 20° C. was added 0-anisaldehyde (399 mg, 2.93 mmol) and a catalytic amount of p-toluenesulfonic acid (10 mg, 0.059 mmol). The resulting solution was then heated to reflux under Dean-Stark trap for 12 hours. The reaction mixture was cooled to 20° C. and diluted with ethyl acetate. The mixture was then partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was washed 3× with NaHCO3, 1× with water, 1× with brine and then dried over anhydrous Na2SO4, filtered and evaporated to dryness. 1.08 g of pale yellow sticky solid was obtained. The resulting crude material was used without further purification.

Workup

  1. temperatureThe resulting solution was then heated
  2. temperatureto reflux under Dean-Stark trap for 12 hours
  3. customThe mixture was then partitioned between ethyl acetate and aqueous sodium bicarbonate
  4. washThe organic phase was washed 3× with NaHCO3, 1× with water, 1× with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c006f955b485415fa39bb35786146658
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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