1,3-Dibromo-5,5-dimethylhydantoin → 6-(Bromomethyl)-3-pyridinecarboxylic acid

HRID 906914Notes

Reaction equation

HRID 906914 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[Br:11]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1>[Br:11][CH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 1378606-Methylnicotinic acid

Product 1

HCID 218409786-(Bromomethyl)-3-pyridinecarboxylic acidYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1st step: To a stirred suspension of 6-methylnicotinic acid (commercially available) (500 mg, 3.64 mmol) in THF (14 mL) at RT, was added 1,3-dibromo-5,5-dimethylhydantoin (DDH) (1.06 g, 3.71 mmol). Stirring was continued over night and concentrated under vacuo. Column chromatography (SiO2, CH2Cl2/MeOH: 8/2) yielded 410 mg (52%) of 6-bromomethyl-nicotinic acid as a light orange solid. ES-MS m/e: 214.2-216.3 (M+H+).

Workup

  1. waitwas continued over night
  2. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-487b45c6299845e2ba2aba2d987137f7
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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