Dimethylformamide dimethyl acetal → [(E)-2-(3-Bromo-2-methoxy-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine

HRID 1909068Notes

Reaction equation

HRID 1909068 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[CH3:8].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1/[CH:8]=[CH:16]/[N:17]([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 665992573-Bromo-2-methoxy-4-methyl-5-nitropyridine

Product 1

HCID 86664356[(E)-2-(3-Bromo-2-methoxy-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-Bromo-2-methoxy-4-methyl-5-nitro-pyridine (3.00 g, 12.1 mmol) in DMF (0.6M) was added via syringe N,N-dimethylformamide-dimethylacetal (3.0 mL, 22.4 mmol, 1.8 eq) in a fast dropwise manner. The solution was heated for 2 hr at 90° C., cooled to 23° C., then diluted with Ethyl Acetate (200 mL). The washed reaction mixture was washed with water, brine, dried (Na2SO4), and concentrated giving [(E)-2-(3-Bromo-2-methoxy-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine as a red solid which was used without further purification (3.45 g, 10.9 mmol, 89%). MS ESI m/z 304.2 (M+2H)+. 1NMR (400 MHz, CDCl3) δ 8.36 (s, 1H), 7.03 (d, J=13.5 Hz, 1H), 5.30 (d, J=13.5 Hz, 1H), 4.05 (s, 3H), 2.97 (s, 3H).

Workup

  1. temperaturecooled to 23° C.
  2. customThe washed reaction mixture
  3. washwas washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1896b3a5928948ce8b80aa1249b298a6
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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