Water → 5-Bromo-4-[2-(dimethylamino)ethenyl]-2-methoxy-3-nitropyridine

HRID 632737Notes

Reaction equation

HRID 632737 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C[O-].[Li+].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21].O>CN(C)C=O>[Br:1][C:2]1[C:3](/[CH:13]=[CH:19]/[N:20]([CH3:22])[CH3:21])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 4177230Lithium methanolateHCID 407869095-Bromo-2-methoxy-3-nitro-4-picoline

Product 1

HCID 578831255-Bromo-4-[2-(dimethylamino)ethenyl]-2-methoxy-3-nitropyridineYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-2-methoxy-4-methyl-3-nitropyridine (15.0 g, 60.7 mmol) was dissolved in dimethylformamide (300 mL), and lithium methanolate (6.07 mL, 6.07 mmol, 1 M) was added. The reaction mixture was heated to 100° C. To this mixture was added 1,1-dimethoxy-N,N-dimethylmethanamine (64.5 mL, 486 mmol) over 10 minutes. The reaction mixture was stirred at 95° C. for 16 hours. The reaction mixture was cooled to room temperature and water was added carefully (300 mL, exothermic). The resulting precipitate was collected by vacuum filtration, washed with water, and dried to provide (E)-2-(5-bromo-2-methoxy-3-nitropyridin-4-yl)-N,N-dimethylethenamine (13.9 g, 45.9 mmol, 76% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-6464814717f34c899d589c684c1a822f
Source dataset
uspto-grants-2016_04
Patent number
US09321765B2

Reaction notes

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