Chlorosuccinimide → 2-Amino-3-chloro-5-cyanopyridine

HRID 2396314Notes

Reaction equation

HRID 2396314 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[Cl:10]N1C(=O)CCC1=O.ClNC1C=CC(C#N)=CN=1>C(#N)C>[NH2:1][C:2]1[C:7]([Cl:10])=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 8182602-Amino-5-cyanopyridineHCID 18988868HCID 18988868, compound

Product 1

HCID 14828812-Amino-3-chloro-5-cyanopyridineYield 89.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Into a 500 ml four-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 6.0 g (0.05 mol) of 2-amino-5-cyanopyridine, 8.3 g (0.0625 mol) of N-chlorosuccinimide and 200 g of acetonitrile were added, and the reaction was conducted at 50° C. for one hour with stirring. During the reaction, the reaction product was analyzed by liquid chromatography, whereby formation of 2-chloroamino-5-cyanopyridine was confirmed. After completion of the reaction, acetonitrile was distilled off. To separate succinimide and the desired product, 50 g of water was added to the remaining product, and the mixture was stirred. Precipitated crystals were collected by filtration, washed with 50 g of toluene and dried to obtain 6.9 g of 2-amino-3-chloro-5-cyanopyridine as slightly brown crystals (purity as measured by liquid chromatography: 98%, yield: 88%).

Workup

  1. customInto a 500 ml four-necked flask equipped with a stirrer
  2. customDuring the reaction
  3. distillationwas distilled off
  4. customTo separate succinimide
  5. additionthe desired product, 50 g of water was added to the remaining product
  6. stirringthe mixture was stirred
  7. customPrecipitated crystals
  8. filtrationwere collected by filtration
  9. washwashed with 50 g of toluene
  10. customdried

Sources & evidence

ORD record
ord-6ff0f960324946a18ea139e8a7686460
Source dataset
uspto-grants-1996_02
Patent number
US05491239

Reaction notes

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