4-(Trifluoromethyl)phenylacetonitrile → HCID 58007561, compound

HRID 1094439Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.CCN(CCCC(N[C:25]1[CH:26]=[C:27](/C=C/C2C=CC=CC=2Cl)[N:28]=[C:29]2[CH:34]=[C:33](Cl)[CH:32]=[CH:31][C:30]=12)C)CC.C([O-])=O.[NH4+]>CO.[Pd]>[N:28]1[C:29]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[C:26]([NH:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:13])[F:1])=[CH:8][CH:7]=2)[CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 10.4 mmol 4-(trifluoromethyl)phenylacetonitrile (commercially available) and 3.5 eq. aminoquinoline in MeOH (10 mL) was treated with ammonium formate (5 eq.) and 10% Pd/C (100 mg) and stirred at 80° C. for 2 h. Filtration, concentration and purification by chromatography (SiO2, CH2Cl2/MeOH) afforded the title compound (73%) as a yellow oil. MS m/e: 317.1 [M+H]+.

Workup

filtrationFiltration, concentration and purification by chromatography (SiO2, CH2Cl2/MeOH)

Sources & evidence

ORD record: ord-96af17530c27410d82d9e47b838b06ca
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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