Acetic Acid → 6-Chloropyridine-2,3-diamine

HRID 427258Notes

Reaction equation

HRID 427258 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[N:11]=[C:10]([NH2:12])[C:9]([N+:13]([O-])=O)=[CH:8][CH:7]=1.[OH-].[NH4+]>[Fe].O>[Cl:5][C:6]1[N:11]=[C:10]([NH2:12])[C:9]([NH2:13])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 106306156-Chloropyridine-2,3-diamineYield 86%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

4.484 g of iron powder is added to a solution containing 78 ml of acetic acid and 3.415 g of 6-chloro-3-nitro-2-pyridinamine. The reaction medium is heated at 60° C.-70° C. for 2 hours 45 minutes, then left to return to ambient temperature. After pouring into 200 ml of water, 200 ml of ammonium hydroxide is added until pH9 is achieved, followed by extraction with ethyl acetate, drying, filtering and concentrating. 3.14 g of crude product is obtained which is chromatographed on silica eluting with an ethyl acetate triethylamine mixture 95/5. 2.43 g of sought product is obtained.

Workup

  1. temperatureThe reaction medium is heated at 60° C.-70° C. for 2 hours 45 minutes
  2. waitleft
  3. customto return to ambient temperature
  4. additionis added until pH9
  5. extractionfollowed by extraction with ethyl acetate
  6. customdrying
  7. filtrationfiltering
  8. concentrationconcentrating
  9. custom3.14 g of crude product is obtained which
  10. customis chromatographed on silica eluting with an ethyl acetate triethylamine mixture 95/5

Sources & evidence

ORD record
ord-2f540a77bafa419c937e038b57f8fec9
Source dataset
uspto-grants-2001_11
Patent number
US06313101B1

Reaction notes

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