m-Chloroperbenzoic acid → HCID 54429926, compound

HRID 1200040Notes

Reaction equation

HRID 1200040 reaction equation
Cl.[CH:2]1([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[C:14]([C:13]1[CH:12]=[N+:11]([O-:25])[CH:10]=[CH:9][C:8]=1[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70043440HCID 70043440, compound

Product 1

HCID 54429926HCID 54429926, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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. customThe precipitate obtained
  2. filtrationis filtered
  3. customthe filtrate evaporated to dryness
  4. filtrationThe precipitate is filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-b30c75d4c69e44cf920e9f1ac4f66c97
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

Loading…