Acetic Acid → 2-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]ethanamine acetate

HRID 2100684Notes

Reaction equation

HRID 2100684 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][C:13]#[N:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:15]([OH:18])(=[O:17])[CH3:16]>[Pd]>[C:15]([OH:18])(=[O:17])[CH3:16].[Cl:1][C:2]1[C:3]([CH2:12][CH2:13][NH2:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 16227272[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]acetonitrile2×

Product 1

HCID 690470172-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]ethanamine acetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

113 g of [3-chloro-5-(trifluoromethyl)-2-pyridinyl]acetonitrile (0.51 mol, 1 eq.) are diluted in 2.5 L of acetic acid. 30 g of palladium (5% on charcoal) are added. The reaction medium is stirred at ambient temperature under a hydrogen pressure of 5 bar. The progress of the reaction is followed by TLC; when the [3-chloro-5-(trifluoromethyl)-2-pyridinyl]acetonitrile has been completely used up, the medium is filtered over a bed of celite, and then concentrated to dryness so as to produce the 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethanamine acetate.

Workup

  1. filtrationthe medium is filtered over a bed of celite
  2. concentrationconcentrated to dryness so as

Sources & evidence

ORD record
ord-50ff42d905544e00b2130beb9d36a904
Source dataset
uspto-grants-2009_08
Patent number
US07572818B2

Reaction notes

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