6-Chloro-3-nitropyridine-2-carbonitrile → 6-Chloro-3-nitropicolinamide

HRID 2359438Notes

Reaction equation

HRID 2359438 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.Cl[Sn]Cl.[OH2:16]>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:9])=[O:16])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 133817056-Chloro-3-nitropyridine-2-carbonitrileHCID 43835034Tin dichloride dihydrate

Product 1

HCID 105360876-Chloro-3-nitropicolinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 6-chloro-3-nitropicolinonitrile (12 g, 65.4 mmol) and SnCl2.H2O (59 g, 262 mmol) in ethanol (144 ml) was heated to 85° C. for 3 hours. The solution was concentrated under reduced pressure, water was added and a saturated aqueous solution of sodium bicarbonate was added until pH=8. The mixture was extracted with ethyl acetate several times. The combined organic layers were dried (Na2SO4), and concentrated under reduce pressure to afford 6-chloro-3-nitropicolinamide in quantitative yield.

Workup

  1. concentrationThe solution was concentrated under reduced pressure, water
  2. additionwas added
  3. additiona saturated aqueous solution of sodium bicarbonate was added until pH=8
  4. extractionThe mixture was extracted with ethyl acetate several times
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bfe570b30afa40a9bb7ef0f597f0107f
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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