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

HRID 2274452Notes

Reaction equation

HRID 2274452 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]>>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:14][CH2:12][CH3:13])[N:10]=1

Participants

3

Reactant 2

HCID 6341EthylamineHCID 8540472,6-Dichloronicotinic acid

Product 1

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

Procedure

A solution of 18.0 g (84.4 mmol) of 2,6-dichloronicotinic acid in 180 ml of a solution of ethylamine (70% in water) was stirred at ambient temperature for 72 hours. The excess amine was then evaporated off under reduced pressure, and an aqueous solution of acetic acid at 10% was added until the product precipitates. The beige solid was spin-filter-dried, rinsed with cold water and dried in an oven. 10.5 g of the expected product are obtained.

Workup

  1. customThe excess amine was then evaporated off under reduced pressure
  2. additionan aqueous solution of acetic acid at 10% was added until the product
  3. customprecipitates
  4. customThe beige solid was spin-filter-dried
  5. washrinsed with cold water
  6. customdried in an oven

Sources & evidence

ORD record
ord-adfeeab2af48490fa71ae6179cb6f4b1
Source dataset
uspto-grants-2015_09
Patent number
US09126972B2

Reaction notes

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