Triethylamine → HCID 59754301, compound

HRID 501574Notes

Reaction equation

HRID 501574 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N+:10]([O-])=[CH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C[Si]([C:19]#[N:20])(C)C.CCN(CC)CC>CC#N>[C:19]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1)#[N:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 836466-Nitroquinoline N-oxide

Product 1

HCID 59754301HCID 59754301, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of compound 45A (400 mg, 2.1 mmol) in MeCN (15 mL) was added trimethylsilylcyanide (0.34 mL, 2.5 mmol), followed by a slow addition of Et3N (0.65 mL, 4.6 mmol). The reaction mixture was heated to 75° C. for 30 min, then cooled to rt, concentrated, dried under vacuum, and purified by silica gel flash chromatography, eluting with CH2Cl2 to give the title compound (150 mg, 36%) as a white solid. LC/MS m/z 200 [M+H]+.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. customdried under vacuum
  4. custompurified by silica gel flash chromatography
  5. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-ae5347965205493caae7ae403dcb3b44
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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