Hydrochloric Acid → 1-(3,5-Difluoropyridin-2-yl)methanamine hydrochloride

HRID 1664154Notes

Reaction equation

HRID 1664154 reaction equation
[F:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.[ClH:11]>[Pd].C(O)C.O1CCCC1>[ClH:11].[F:1][C:2]1[C:3]([CH2:9][NH2:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 27832532-Cyano-3,5-difluoropyridine

Product 1

HCID 210698531-(3,5-Difluoropyridin-2-yl)methanamine hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of 3,5-difluoropicolinonitrile (1.4 g, 10 mmol), conc. HCl (12 ml) and 10% Pd—C (200 mg) in 1:1 ethanol/tetrahydrofuran was shaken under a hydrogen atmosphere (50 psi) for 5 h. The reaction mixture was filtered and the ethanol removed in vacuo. The remaining solution was lyophilized to afford an off-white solid (2.16 g, 100% yield). LCMS (M+H) calcd for C6H7F2N2: 145.06; found: 145.12.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe ethanol removed in vacuo

Sources & evidence

ORD record
ord-19d7ef61500c40f1b39b9f6aa2c6bb09
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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