Ammonium Chloride → 3-Amino-6-chloropyridine-2-carboxamide

HRID 1045996Notes

Reaction equation

HRID 1045996 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[O:9])[C:5]([N+:11]([O-])=O)=[CH:4][CH:3]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:11][C:5]1[C:6]([C:8]([NH2:10])=[O:9])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 105360876-Chloro-3-nitropicolinamide

Product 1

HCID 107497043-Amino-6-chloropyridine-2-carboxamide

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

6-chloro-3-nitro-pyridine-2-carboxylic acid amide (10.43 g, 51.75 mmol) is taken up in EtOH (250 mL), combined with ammonium chloride (1.384 g, 25.87 mmol) in water (250 mL) and heated to 60° C. At this temperature iron powder (8.67 g, 155.23 mmol) is added batchwise and the mixture is stirred for 1 h at 60° C. After cooling it is concentrated by rotary evaporation, filtered through silica gel, washed with DCM/MeOH (90/10 to 80/20), the resulting filtrate is evaporated down using the rotary evaporator and 3-amino-6-chloro-pyridine-2-carboxylic acid amide (HPLC-MS: tRet.=0.90 min; MS (M+H)+=172) is obtained.

Workup

  1. temperatureAfter cooling it
  2. concentrationis concentrated by rotary evaporation
  3. filtrationfiltered through silica gel
  4. washwashed with DCM/MeOH (90/10 to 80/20)
  5. customthe resulting filtrate is evaporated down
  6. customthe rotary evaporator

Sources & evidence

ORD record
ord-6f1dac53361e45bc8ce06dace76dbf4f
Source dataset
uspto-grants-2013_10
Patent number
US08569316B2

Reaction notes

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