Pyridine → 2-Bromo-N-methoxy-N-methylisonicotinamide

HRID 414923Notes

Reaction equation

HRID 414923 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](O)=[O:6].Cl.[CH3:12][NH:13][O:14][CH3:15].CN(C)CCCN=C=NCC.N1C=CC=CC=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([N:13]([O:14][CH3:15])[CH3:12])=[O:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2227012-Bromoisonicotinic acid

Product 1

HCID 448186542-Bromo-N-methoxy-N-methylisonicotinamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a round-bottomed flask, 2.0 g of 2-bromoisonicotinic acid, 1.1 g of N,O-dimethylhydroxylamine hydrochloride, 3.8 g of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide and 3.2 ml of pyridine are placed in 50 ml of tetrahydrofuran. The mixture is stirred at ambient temperature for 40 h. The mixture is concentrated, and the residue is taken up in 50 ml of ethyl acetate and 50 ml of water. The organic phase is washed with 50 ml of a 1N solution of sodium hydroxide and 50 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and then concentrated under reduced pressure. 2.0 g of compound are obtained.

Workup

  1. concentrationThe mixture is concentrated
  2. washThe organic phase is washed with 50 ml of a 1N solution of sodium hydroxide and 50 ml of a saturated solution of sodium chloride
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a83387cdb3d04fc18f5c12294af90f82
Source dataset
uspto-grants-2012_01
Patent number
US08088765B2

Reaction notes

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