1,1-Dimethoxyethyl(dimethyl)amine → N-(1-dimethylaminoethylidene)-5-ethyl-6-methoxy-2-methylnicotinamide

HRID 1921363Notes

Reaction equation

HRID 1921363 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[C:17](OC)([N:19]([CH3:21])[CH3:20])[CH3:18]>>[CH3:20][N:19]([CH3:21])[C:17](=[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])[CH3:18]

Participants

3

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 674926225-Ethyl-6-methoxy-2-methyl-nicotinamide

Product 1

HCID 67492454N-(1-dimethylaminoethylidene)-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 (195 mg, 1.00 mmol) of Step 1, Example 16 is treated with dimethylacetamide dimethylacetal (2 mL). The mixture is stirred at 100° C. for 65 min to give a dark solution. The reaction mixture is evaporated to give N-(1-dimethylaminoethylidene)-5-ethyl-6-methoxy-2-methylnicotinamide directly as a black oil that is used without purification. MS: m/e=264 (M+H).

Workup

  1. customto give a dark solution
  2. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-e3e7452bf87f42038b249e3b2d53f66a
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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