2,6-Bis(4-(trifluoromethyl)phenyl)-4-pyridinecarbonitrile → [2,6-Bis[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine

HRID 1479836Notes

Reaction equation

[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]#[N:16])[CH:12]=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[N:10]=2)=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[C:13]([CH2:15][NH2:16])[CH:12]=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)[N:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The nitrile 28A (4.7 g, 12 mmol) dissolved in 50 ml of diethyl ether was added dropwise to a mixture of LiAlH4 (912 mg, 2 equiv.) in diethyl ether (80 mL) stirred at 0° C. Then the mixture was stirred at room temperature overnight. The excess of LiAlH4 was destroyed by water addition at 0° C., the solid formed was filtered, washed with Et2O and the filtrate was dried over Na2SO4 and evaporated to dryness to obtain 2.5 g of the amine 29A as yellow solid. Yield=52% 1HNMR (DMSO, 400 MHz) δ 2.25 (2H, bs), 3.90 (2H, s), 7.90 (4H, d, J=8 Hz), 8.11 (2H, s), 8.40 (4H, d, J=8 Hz)

Workup

stirringThen the mixture was stirred at room temperature overnight
customThe excess of LiAlH4 was destroyed by water addition at 0° C.
customthe solid formed
filtrationwas filtered
washwashed with Et2O
dry with materialthe filtrate was dried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-ec5687950bda45588eeb0f184851743d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

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