Hydrochloric Acid → 3-(Aminomethyl)-6-methyl-4-(trifluoromethyl)-1,2-dihydropyridin-2-one hydrochloride HCl salt

HRID 2208657Notes

Reaction equation

[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.N#N.[ClH:17]>CO.[OH-].[OH-].[Pd+2]>[ClH:17].[ClH:17].[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[CH:3][C:4]=1[C:11]([F:12])([F:13])[F:14]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 6-methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile (400 mg, 1.98 mmol) in MeOH (19.8 ml) and HCl (436 ul, 12M) was added 10% Pd(OH)2 (361 mg, 0.257 mmol) under N2 atmosphere. The N2 gas was displaced by H2 gas and the mixture was stirred for 18 h at 23° C. under hydrogen. The H2 gas was displaced by N2 gas. The mixture was filtered through Celite, washed with MeOH and concentrated. The residue was triturated with MeOH-Et2O, collected with Buchner funnel, and dried in vacuo to give the titled compound (433 mg, 100%). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.31 (s, 3H), 3.88 (s, 2H), 6.43 (s, 1H).

Workup

filtrationThe mixture was filtered through Celite
washwashed with MeOH
concentrationconcentrated
customThe residue was triturated with MeOH-Et2O
customcollected with Buchner funnel
customdried in vacuo

Sources & evidence

ORD record: ord-c8703142aed845d78710af68f2150acb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376422B2

Reaction notes

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