Hydrochloric Acid → 3-Amino-6-chloropyridine-2-carbonitrile

HRID 1801483Notes

Reaction equation

HRID 1801483 reaction equation
[C:1]([C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[C:5]([Cl:12])[N:4]=1)#[N:2].Cl>C(O)C>[C:1]([C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[C:5]([Cl:12])[N:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 5927503-Amino-6-chloropyridine-2-carbonitrileYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Added 4 g (21.8 mmol) of 2-cyano-3-nitro-6-chloropyridine into concentrated hydrochloric acid (15.00 mL) and ethanol (45.00 mL), then the solution was stirred thoroughly. 4.27 g (76.3 mmol) of reduced iron powder was added in batches to the mixture under a speed that maintained a slight boiling in the flask. The mixture was heated under reflux for 30 min, poured into ice-water (650 mL), stirred, and filtered. Sufficient aether was added to the filter cake and the mixture was stirred thoroughly and filtered. The filtrate was dried with anhydrous magnesium sulfate. The filtrate was adjusted to alkaline with concentrated ammonia first, then filtered and extracted with ether for 3 times. The combined solution of the organic phase and ether solution was dried with anhydrous magnesium sulfate before combined, and then filtered and evaporated under reduced pressure to yield 2.92 g of yellow solid product with a recovery rate of 87.42%.

Workup

  1. temperaturemaintained a slight boiling in the flask
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 min
  4. stirringstirred
  5. filtrationfiltered
  6. additionSufficient aether was added to the filter cake
  7. stirringthe mixture was stirred thoroughly
  8. filtrationfiltered
  9. dry with materialThe filtrate was dried with anhydrous magnesium sulfate
  10. filtrationfiltered
  11. extractionextracted with ether for 3 times
  12. dry with materialThe combined solution of the organic phase and ether solution was dried with anhydrous magnesium sulfate
  13. filtrationfiltered
  14. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7637ae77faf64bc582b28e25b25dd247
Source dataset
uspto-grants-2013_01
Patent number
US08349835B2

Reaction notes

Loading…