Ethylamine → 6-Chloro-2-(ethylamino)nicotinic acid

HRID 2088855Notes

Reaction equation

HRID 2088855 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12]([NH2:14])[CH3:13]>O>[Cl:11][C:9]1[N:10]=[C:2]([NH:14][CH2:12][CH3:13])[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 633764796-Chloro-2-(ethylamino)nicotinic acidYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 18.0 g (84.4 mmol) of 2,6-dichloronicotinic acid in 180 ml (3.45 mol) of a 70% solution of ethylamine in water is heated at 50° C. for ten hours. The excess amine is then evaporated off under reduced pressure, and aqueous 10% acetic acid solution is then added until the product precipitates. The beige-coloured solid is filtered off by suction, rinsed with cold water and oven-dried. 10.5 g of the expected product are obtained. Yield=62%. Melting point: 158-160° C.

Workup

  1. customThe excess amine is then evaporated off under reduced pressure, and aqueous 10% acetic acid solution
  2. additionis then added until the product
  3. customprecipitates
  4. filtrationThe beige-coloured solid is filtered off by suction
  5. washrinsed with cold water
  6. customoven-dried

Sources & evidence

ORD record
ord-6d0bf55481e1477d9c07f0ae0ce7a5f7
Source dataset
uspto-grants-2013_05
Patent number
US08436011B2

Reaction notes

Loading…