Ammonia → 2-Amino-6-chloronicotinic acid

HRID 77844

Reaction equation

HRID 77844 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]>>[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

3

Reactant 2

HCID 222AmmoniaHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 122639922-Amino-6-chloronicotinic acidYield 49%

Conditions

Temperature
135 °C

Procedure

A mixture of 2,6-dichloro-nicotinic acid (31 g, 0.14 mol) and 28% aqueous ammonia solution (200 mL) was stirred in a sealed tube for 10 hours at 135° C. This reaction solution was cooled to room temperature, and the excess ammonia gas was removed under a reduced pressure. Water was added to the residue to a total of 1000 mL, the mixture was cooled to 0° C., and citric acid was added to a pH being about 6. The precipitated solids were filtered out to obtain the title compound (12 g, 49%).

Workup

  1. temperatureThis reaction solution was cooled to room temperature
  2. customthe excess ammonia gas was removed under a reduced pressure
  3. additionWater was added to the residue to a total of 1000 mL
  4. temperaturethe mixture was cooled to 0° C.
  5. additioncitric acid was added to a pH
  6. filtrationThe precipitated solids were filtered out

Sources & evidence

ORD record
ord-c6bcdac826aa4bd2aef409a03fd677ce
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Linked notes

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