Ethylamine → 2-(Aminoethyl)-6-chloronicotinic acid

HRID 1260572Notes

Reaction equation

HRID 1260572 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>[NH2:14][CH2:12][CH2:13][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 866423332-(Aminoethyl)-6-chloronicotinic 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 solution of ethylamine at 70% in water is stirred at ambient temperature for 72 hours. The excess amine is then evaporated off under reduced pressure, and an aqueous solution of acetic acid at 10% is then added until the product precipitates. The beige solid is spin-filter-dried, 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 off under reduced pressure
  2. additionan aqueous solution of acetic acid at 10% is then added until the product
  3. customprecipitates
  4. customThe beige solid is spin-filter-dried
  5. washrinsed with cold water
  6. customdried in an oven

Sources & evidence

ORD record
ord-907d02bcd16f4dc48ddd53bccbc9514c
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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