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

HRID 1517427Notes

Reaction equation

HRID 1517427 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-])=O)=[CH:4][CH:3]=1.C(O)(=O)C.[O-]S(S([O-])=O)=O.[Na+].[Na+].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[NH2:10][C:5]1[C:6]([C:8]#[N:9])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14812Phosphorus oxide (P4O10)HCID 24489Sodium DithioniteHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 5927503-Amino-6-chloropyridine-2-carbonitrileYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 6-chloro-3-nitro-pyridine-2-carbonitrile (5.5 g, 30 mmol) in water (100 ml), was added acetic acid (5.4 ml, 90 mmol). The mixture was stirred at room temperature for 20 minutes. Then, Na2S2O4 (20 g, 86%, 90 mmol) was added slowly. The reaction mixture was stirred at room temperature for another 2 hours. The precipitate was filtered off and washed with cold water (2×10 ml). The precipitate was dried over P2O5 yielding the title compound as a yellowish solid (3.7 g, yield: 80%) which was characterised as follows:

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 2 hours
  2. filtrationThe precipitate was filtered off
  3. washwashed with cold water (2×10 ml)

Sources & evidence

ORD record
ord-35e062a7687e45758a82e9a06f4508d2
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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