Chlorotrimethylsilane → HCID 19864584, compound

HRID 1200041Notes

Reaction equation

HRID 1200041 reaction equation
[C:1]([C:4]1[CH:5]=[N+:6]([O-])[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([OH:3])=[O:2].[C-]#N.[Na+].[CH2:20]([N:22](CC)CC)C.Cl[Si](C)(C)C>CN(C)C=O>[C:1]([C:4]1[C:9]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:8][C:7]([C:20]#[N:22])=[N:6][CH:5]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 8929Sodium CyanideHCID 54429926HCID 54429926, compound

Product 1

HCID 19864584HCID 19864584, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Cyclohexylnicotinic acid hydrochloride (4.5 g, 0.018 mol) is dissolved in methylene chloride (40 ml). This solution is mixed with a cold solution of metachloroperbenzoic acid (10.82 g, 0.063 mol) in CH2Cl2 (80 ml), and the resulting mixture is stirred at room temperature overnight. The precipitate obtained is filtered and the filtrate evaporated to dryness. The residue is suspended in ether. The precipitate is filtered, washed with ether and dried to yield 3-carboxy-4-cyclohexyl-pyridine N-oxide, m.p. 168°-169°. (c) To a solution of 3-carboxy-4-cyclohexyl-pyridine N-oxide (3.09 g, 0.014 mol), sodium cyanide (2.47 g, 0.05 mol) and triethylamine (7.08 g, 0.07 mol) in absolute dimethylformamide (50 ml), chlorotrimethylsilane (7.6 g, 0.07 mol) is added. The reaction mixture is then heated for 28 h at 85°. After cooling, the inorganic salts are filtered, washed with diethyl ether, and the filtrate is evaporated at 50° in vacuo. The dark residue is purified by chromatography on Florisil® (ethyl acetate/methanol 4:1) to yield 5-carboxy-2-cyano-4-cyclohexyl-pyridine; m.p. 225°-230°, Rf =0.55.

Workup

  1. temperatureThe reaction mixture is then heated for 28 h at 85°
  2. temperatureAfter cooling
  3. filtrationthe inorganic salts are filtered
  4. washwashed with diethyl ether
  5. customthe filtrate is evaporated at 50° in vacuo
  6. customThe dark residue is purified by chromatography on Florisil® (ethyl acetate/methanol 4:1)

Sources & evidence

ORD record
ord-97d31bf716134dff8c0fe7f06d610f3e
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

Loading…