Dimethylamine → 6-bromo-N,N-dimethylpyridin-2-amine

HRID 2079751Notes

Reaction equation

HRID 2079751 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH3:9][NH:10][CH3:11]>C(O)C>[Br:1][C:2]1[N:3]=[C:4]([N:10]([CH3:11])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 122742,6-Dibromopyridine

Product 1

HCID 140060626-bromo-N,N-dimethylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a stirred mixture of 2,6-dibromopyridine (15; g, 63; mmol) and dimethylamine (40% aqueous solution, 21.4; mL, 190; mmol, 3; equiv) in ethanol (75; mL) for 3; days at 70° C. Evaporate the yellow solution to a reduced volume and dilute with ethyl acetate (100; mL). Wash with water (40; mL), brine (40; mL) and dry over sodium sulfate. Decant the liquid and evaporate to give pale yellow oil (13.8; g). Distill using a Kügelrohr apparatus to give the title product as a colorless liquid (12.4; g, b.p.=100-140° C. at 0.1 mbar). MS (m/z): 201, 203; (M+1).

Workup

  1. temperatureHeat
  2. customat 70° C
  3. customEvaporate the yellow solution to a reduced volume
  4. additiondilute with ethyl acetate (100; mL)
  5. washWash with water (40; mL), brine (40; mL)
  6. dry with materialdry over sodium sulfate
  7. customDecant the liquid
  8. customevaporate
  9. customto give pale yellow oil (13.8; g)
  10. distillationDistill

Sources & evidence

ORD record
ord-0614a712d8d04dc8beedf7e13ed36430
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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