2-Cyano-4-methylpyridine → (4-Methylpyridin-2-yl)methanamine

HRID 1042362Notes

Reaction equation

HRID 1042362 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1)#[N:2]>CO.Cl>[CH3:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:1][NH2:2])[CH:8]=1

Participants

4

Reactant 1

HCID 887392-Cyano-4-methylpyridine

Product 1

HCID 15144432(4-Methylpyridin-2-yl)methanamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

2-Cyano 4-methylpyridine in MeOH (35 ml) and concentrated HCl (1 ml) was stirred under a H2 balloon for 14 hours. The reaction mixture was filtered and concentrated. The pH was adjusted to 12 by the addition of aq sodium hydroxide. The resulting reaction mixture was extracted with dichloromethane several times. Concentration of the solvent gave the crude title compound, which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additionThe pH was adjusted to 12 by the addition of aq sodium hydroxide
  4. customThe resulting reaction mixture
  5. extractionwas extracted with dichloromethane several times

Sources & evidence

ORD record
ord-6fee6649a7bd45e6bda5c248e6a11dfa
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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