Methanol → 2-Bromo-isonicotinic acid methyl ester

HRID 1892599Notes

Reaction equation

HRID 1892599 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].CO.Cl.[CH2:14](N=C=NCCCN(C)C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([O:7][CH3:14])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 2227012-Bromoisonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 38477682-Bromo-isonicotinic acid methyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of 2-bromoisonicotinic acid (73 g, 0.361 mol) in dichloromethane (500 mL) and methanol (35 g, 1.08 mol) was added 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (67 g, 0.434 mol) by portions. The mixture was stirred at ambient temperature overnight. Then 120 g silica gel was added and the solvent evaporated. The residue was purified by flash chromatography, eluting with 5% ethyl acetate in petroleum ether to afford 58 g (75%) of methyl 2-bromoisonicotinate as a white solid.

Workup

  1. additionThen 120 g silica gel was added
  2. customthe solvent evaporated
  3. customThe residue was purified by flash chromatography
  4. washeluting with 5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-481ac5a24f0446e889d7cc85adc9dcdb
Source dataset
uspto-grants-2013_08
Patent number
US08507681B2

Reaction notes

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