2,5-Dibromopyridine → 5-Bromo-N-(2,2-dimethoxyethyl)pyridin-2-amine

HRID 1792456Notes

Reaction equation

HRID 1792456 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH2:18]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:18][CH2:17][CH:16]([O:19][CH3:20])[O:15][CH3:14])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 693532,5-DibromopyridineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 516892Sodium Bicarbonate

Product 1

HCID 164142515-Bromo-N-(2,2-dimethoxyethyl)pyridin-2-amine

Procedure

After 50 g of 2,5-dibromopyridine and 50 mL aminoacetaldehyde dimethyl acetal were heated at 130° C. for 8 hours, an aqueous saturated sodium bicarbonate solution was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with brine, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane), to give 23.53 g of the title compound (pale yellow oil).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7826fd182752414c9f1a1263d827f13b
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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