Ammonia → 2-Amino-6-chloronicotinic acid

HRID 1171192Notes

Reaction equation

HRID 1171192 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
115 °C

Procedure

2,6-Dichloronicotinic acid (0.38 g, 2 mmol) and copper (I) iodide (720 mg, 3.8 mmol) were added to liquid ammonia (approx. 20 mL) in a sealed tube at −78° C., which was heated for 25 hours (oil bath temperature: 115° C.). The oil bath temperature was raised to 125° C. followed by additionally heating for 14 hours 30 minutes. The reaction mixture was allowed to return to room temperature followed by distilling off the ammonia. The insoluble material that precipitated following addition of methanol was filtered out and the filtrate was concentrated to obtain the title compound (0.25 g, 1.45 mmol, 72%) as a solid.

Workup

  1. temperatureThe oil bath temperature was raised to 125° C.
  2. temperatureby additionally heating for 14 hours 30 minutes
  3. customto return to room temperature
  4. distillationby distilling off the ammonia
  5. customThe insoluble material that precipitated
  6. additionaddition of methanol
  7. filtrationwas filtered out
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-858ffd9ac2b0430bb03a35123145d580
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

Loading…