Bromine → 2-Amino-5-bromo-3-pyridinecarbaldehyde

HRID 2054464Notes

Reaction equation

HRID 2054464 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:10]Br>C(OCC)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([Br:10])=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 242137922-Amino-5-bromo-3-pyridinecarbaldehydeYield 88.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2-aminopyridine-3-carboxaldehyde (10 g, 81.88 mmol) in dry diethyl ether, bromine (5.45 ml, 106.44 mmol) was added drop-wise. The reaction was stirred at ambient temperature for 30 min. The amber solids were filtered and dissolved in ethyl acetate. The ethyl acetate solution was washed with 1 N NaOH and then brine, dried over anhydrous Na2SO4 and filtered. The solvent was evaporated to afford 2-amino-5-bromonicotinaldehyde (14.6 g, 88% yield).

Workup

  1. filtrationThe amber solids were filtered
  2. dissolutiondissolved in ethyl acetate
  3. washThe ethyl acetate solution was washed with 1 N NaOH
  4. dry with materialbrine, dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8b4d6f3f55684ac3b78e34bf3b8d3d97
Source dataset
uspto-grants-2008_02
Patent number
US07329678B2

Reaction notes

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