Hydrochloric Acid → (6-Chloro-2-methylpyridin-3-YL)methanamine

HRID 241689Notes

Reaction equation

HRID 241689 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[N:3]=1.[BH4-].[Na+].B(F)(F)F.Cl>C1COCC1.CO>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[C:5]([CH2:6][NH2:7])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6356Boron trifluorideHCID 4311764Sodium borohydrideHCID 123877376-Chloro-2-methylnicotinonitrile

Product 1

HCID 59534442(6-Chloro-2-methylpyridin-3-YL)methanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-Chloro-2-methyl-nicotinonitrile (6 g) in THF (120 ml) at 25° C. was added NaBH4 (3 g) followed by the dropwise addition of BF3 etherate (6 ml). The reaction mixture was stirred for 3 h. MeOH (100 ml) and 2N HCl (100 ml) was added and refluxed for 1 h. The organic solvent was removed in vacuum and conc. NaOH (40 ml) was added followed by extraction with diethyl ether. The organic layer was separated, dried and concentrated in vacuum followed by filtration over silica gel (EtOAc/MeOH 80:20). The title compound was crystallized from MeOH/HCl (5.5 g)

Workup

  1. temperaturerefluxed for 1 h
  2. customThe organic solvent was removed in vacuum and conc. NaOH (40 ml)
  3. additionwas added
  4. extractionfollowed by extraction with diethyl ether
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated in vacuum
  8. filtrationfollowed by filtration over silica gel (EtOAc/MeOH 80:20)
  9. customThe title compound was crystallized from MeOH/HCl (5.5 g)

Sources & evidence

ORD record
ord-5b72cf9b45d1488ab094354e00ccb3ff
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

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