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

HRID 2383231Notes

Reaction equation

HRID 2383231 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>[CH2:12]([NH:14][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH3:13]

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 of a 70% solution of ethylamine in water is stirred at ambient temperature for 72 hours. The excess amine is then evaporated under reduced pressure and then a 10% aqueous acetic acid solution is added until the product precipitates. The beige solid is filtered off, rinsed with cold water and dried in an oven. 10.5 g of the expected product are obtained. Melting point: 158-160° C. Yield=62%.

Workup

  1. customThe excess amine is then evaporated under reduced pressure
  2. additiona 10% aqueous acetic acid solution is added until the product
  3. customprecipitates
  4. filtrationThe beige solid is filtered off
  5. washrinsed with cold water
  6. customdried in an oven

Sources & evidence

ORD record
ord-ef9eb3155dc7427da741001ef2a06ed8
Source dataset
uspto-grants-2012_09
Patent number
US08263614B2

Reaction notes

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