Trimethylamine → HCID 57458161, compound

HRID 1924793Notes

Reaction equation

HRID 1924793 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N+:11]([O-])=[CH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C[Si]([C:20]#[N:21])(C)C.CN(C)C>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:20]#[N:21])[CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 82115Trimethylsilyl cyanideHCID 66637270HCID 66637270, compound

Product 1

HCID 57458161HCID 57458161, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-tert-butylquinoline 1-oxide (310 mg, 1.54 mmol), trimethylsilylcyanide (458 mg, 4.62 mmol), trimethylamine (312 mg, 3.08 mmol) in acetonitrile (3 ml) was stirred for 15 minutes at 120° C. under microwave irradiation. The mixture was applied to a silica gel column chromatography and eluted with hexane/EtOAc (20:1) to furnish the title compound (295 mg, 91% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.44 (9H, s), 7.68 (1H, d, J=8.8 Hz), 7.79 (1H, d, J=2.2 Hz), 7.94 (1H, d, J=2.2, 8.8 Hz), 8.11 (1H, d, J=8.8 Hz), 8.26 (1H, d, J=8.8 Hz) MS (ESI): m/z 211 (M+H)+.

Workup

  1. washeluted with hexane/EtOAc (20:1)

Sources & evidence

ORD record
ord-12714170f8b24fa6b83dcea484e64de4
Source dataset
uspto-grants-2012_05
Patent number
US08178558B2

Reaction notes

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