Ammonia → 2-Amino-6-chloronicotinic acid

HRID 2079936Notes

Reaction equation

HRID 2079936 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].[NH3:12]>[Cu]I>[NH2:12][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 222AmmoniaHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 122639922-Amino-6-chloronicotinic acidYield 72%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
125 °C

Procedure

To liquid ammonia (approximately 20 mL) was added 2,6-dichloro-nicotinic acid (0.38 g, 2 mmol) and copper(I) iodide (720 mg, 3.8 mmol) at −78° C. in a sealed tube, and the solution was heated for 25 hours (the temperature of the oil bath was 115° C.). The temperature of the oil bath was raised to 125° C., which was further heated for 14 hours 30 minutes. The reaction mixture was allowed to room temperature, and ammonia was evaporated. Methanol was added, insoluble matter was removed by filtration, and the filtrate was concentrated to obtain the title compound (0.25 g, 1.45 mmol, 72%) as a solid.

Workup

  1. temperaturethe solution was heated for 25 hours (the temperature of the oil bath
  2. customwas 115° C.
  3. temperaturewhich was further heated for 14 hours 30 minutes
  4. customwas allowed to room temperature
  5. customammonia was evaporated
  6. additionMethanol was added
  7. custominsoluble matter was removed by filtration
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-786036a2008a42949543a182bc7ab091
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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