HCID 13964476, compound → HCID 86644786, compound

HRID 1400226Notes

Reaction equation

HRID 1400226 reaction equation
[C:1]([C:4]1[N:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].C1C=C[NH+]=CC=1.[Br:20][Br-]Br>Br.C(O)(=O)C>[Br-:20].[Br:20][CH2:2][C:1]([C:4]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=[CH:12][NH+:13]=1)=[O:3]

Participants

4

Reactant 1

HCID 13964476HCID 13964476, compound

Product 1

HCID 86644786HCID 86644786, compoundYield 157.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Procedure

To a solution of methyl 2-acetylnicotinate (750 mg, 4.19 mmol)—prepared according to H. Nagano et al.; Heterocycles 1987, 26, 1263-1270—in 2 ml of 33% HBr in acetic acid a suspension of pyridinium bromide perbromide (1.4 g, 4.38 mmol) in 5 ml of acetic acid was added, and stirred for 5 hours at room temperature. The precipitate formed was filtered off under suction, washed with n-pentane and dried to give 1.17 g of the title compound.

Workup

  1. additionwas added
  2. customThe precipitate formed
  3. filtrationwas filtered off under suction
  4. washwashed with n-pentane
  5. customdried

Sources & evidence

ORD record
ord-f8f62855ae0844bdaec4b39ed7aa5a9f
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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