Dimethylformamide dimethyl acetal → HCID 10923381, compound

HRID 1678242Notes

Reaction equation

HRID 1678242 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH2:11])[CH:3]=1.CO[CH:14]([N:17]([CH3:19])[CH3:18])OC>>[CH3:14][N:17]([CH3:19])/[CH:18]=[CH:1]/[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([N:11]=[CH:14][N:17]([CH3:19])[CH3:18])[CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2431652-Amino-4-methyl-5-nitropyridine

Product 1

HCID 10923381HCID 10923381, compoundYield 101%

Conditions

Temperature
120 °C

Procedure

4-Methyl-5-nitro-pyridin-2-ylamine (Aldrich, 4.80 g, 31.4 mmol) was suspended in dimethoxymethyl-dimethylamine (50 mL) and the mixture was heated at about 120° C. in a sealed vessel with stirring for about 4 days. The reaction was cooled and concentrated to afford N′-[4-((E)-2-Dimethylamino-vinyl)-5-nitro-pyridin-2-yl]-N,N-dimethyl-formamidine (8.36 g, 101%) as a dark solid, RP HPLC (Table 1, Method e) Rt=1.62, m/z: (MH)+ 264. The crude product was then used in the next step without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-88ebe85a2bbe4feea85fa96074c3337a
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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