Dimethylformamide dimethyl acetal → 2-(6-Chloro-3-nitropyridin-2-yl)-N,N-dimethylethen-1-amine

HRID 363323Notes

Reaction equation

HRID 363323 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CN(C)C=O.C(N(CC)CC)C>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 2531236-Chloro-2-methyl-3-nitropyridine

Product 1

HCID 537327152-(6-Chloro-3-nitropyridin-2-yl)-N,N-dimethylethen-1-amine

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5 gm (29 mMol) 6-chloro-3-nitro-2-picoline in 40 mL dimethylformamide was treated with 5.83 mL (44 mMol) dimethylformamide dimethylacetal and the resulting mixture heated at 100° C. for 1.5 hours. At this point, 2 drops of triethylamine followed by 1.9 mL dimethylformamide dimethylacetal were added and heating continued for 2 more hours. The reaction mixture was concentrated under reduced pressure to provide the desired compound.

Workup

  1. additionwere added
  2. temperatureheating
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c41032bbabc94757a6fef27dc577d9cd
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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