Dimethylformamide dimethyl acetal → N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methylnicotinamide

HRID 1921357Notes

Reaction equation

HRID 1921357 reaction equation
[CH2:1]([C:3]1[C:4]([O:13][CH3:14])=[N:5][C:6]([CH3:12])=[C:7]([CH:11]=1)[C:8]([NH2:10])=[O:9])[CH3:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[CH3:17][N:18]([CH:20]=[N:10][C:8](=[O:9])[C:7]1[CH:11]=[C:3]([CH2:1][CH3:2])[C:4]([O:13][CH3:14])=[N:5][C:6]=1[CH3:12])[CH3:19]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 674926225-Ethyl-6-methoxy-2-methyl-nicotinamide

Product 1

HCID 67492560N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methylnicotinamide

Conditions

Temperature
100 °C

Procedure

In a round bottom flask under a nitrogen atmosphere, 5-ethyl-6-methoxy-2-methyl-nicotinamide (60 mg, 0.309 mmol) is treated with dimethylformamide dimethylacetal (0.5 mL). The resulting mixture is stirred at 100° C. for 1.25 hr to give a yellow solution. LC/MS shows the complete consumption of the starting material. The reaction mixture is evaporated to give N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methyl-nicotinamide directly as a cream solid that is used without purification. MS: m/e=250 (M+H); 1H NMR (CDCl3, δ, ppm): 8.57 (1H, s), 8.19 (1H, s), 5.77 (2H, s), 3.98 (3H, s), 3.19 (6H, s), 2.58 (3H, s), 2.56 (2H, q), 1.20 (3H, t).

Workup

  1. customto give a yellow solution
  2. customthe complete consumption of the starting material
  3. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-a89f7ddf16d94f9aa336f1ce9fca6b82
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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