Triethylamine → 2-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridine

HRID 277988Notes

Reaction equation

HRID 277988 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH3:12])[N:4]=1.CO[CH:15](OC)[N:16]([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH:12]=[CH:15][N:16]([CH3:18])[CH3:17])[N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 2304756-Methoxy-2-methyl-3-nitropyridine

Product 1

HCID 544306472-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridineYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To 2-methoxy-5-nitro-6-methylpyridine (29.39 g, 175 mmol) dissolved in 300 mL of N,N-dimethylformamide was added dimethylformamide dimethylacetal (120 mL, 896 mmol) and triethylamine (1 mL). The bright red reaction mixture was heated at 120° C. for 2 hours, then concentrated in vacuo to provide 38.90 g of the title compound as a red solid, which was used in Preparation 13 without further purification.

Workup

  1. customThe bright red reaction mixture
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f064d66dfc6746cabbd94a1f2d1e74bc
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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