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

HRID 467837Notes

Reaction equation

HRID 467837 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 10 hours. The excess amine is then evaporated under reduced pressure, then a 10% aqueous solution of acetic acid is added until the product is precipitated. The beige solid is filtered, rinsed with cold water and stove-dried. 10.5 g of the expected product is obtained. Yield=62%. Melting point: 158-160° C. MH+: 201.1 (Tr: 7.7 min, condition 1).

Workup

  1. customThe excess amine is then evaporated under reduced pressure
  2. additiona 10% aqueous solution of acetic acid is added until the product
  3. customis precipitated
  4. filtrationThe beige solid is filtered
  5. washrinsed with cold water
  6. customstove-dried

Sources & evidence

ORD record
ord-e821ba19d54f4ff68d68ef98db2dfb08
Source dataset
uspto-grants-2014_01
Patent number
US08623893B2

Reaction notes

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