3-Chlorobenzoic Acid → HCID 13340175, compound

HRID 1249619Notes

Reaction equation

HRID 1249619 reaction equation
C1([CH:7]2O[C:15]3[C:10](=[N:11][C:12]([CH:17]=C)=[CH:13][CH:14]=3)[CH2:9][O:8]2)C=CC=CC=1.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([O:28]O)=[O:27])[CH:21]=1.ClC1C=C(C=CC=1)C(O)=[O:35]>C(Cl)Cl>[O:8]1[CH2:7][CH:9]1[C:10]1[N+:11]([O-:35])=[C:12]2[CH2:17][O:27][CH:26]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:20][CH:21]=3)[O:28][C:13]2=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 70297m-Chloroperbenzoic acidHCID 13340174HCID 13340174, compound

Product 1

HCID 13340175HCID 13340175, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 4-neck 500 ml., round bottom flask, fitted with a reflux condenser, a mechanical stirrer/magnetic stirring bar and a thermometer, was placed 2-phenyl-6-vinyl-4H-1,3-dioxino[5,4-b]pyridine (8.0 g., 0.033 mole) in methylene chloride (250 ml.). The solution was treated portion wise with m-chloroperbenzoic acid (20.0 g., 0.116 mole). When all of the peracid was added, the solution was heated at reflux overnight. Upon cooling m-chlorobenzoic acid crystallized from the reaction mixture and was filtered off. The filtrate was washed with aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated in vacuo to give the crude product (5.1 g.) which was recrystallized from ethyl acetate to give 6-(1,2-epoxyethyl)-2-phenyl-4H-1,3-dioxino[5,4-b]pyridine N-oxide (1.9 g., 21%), m.p. 180°-181.5° C. (dec.); NMR (CDCl3) delta 7.28 (m, 5H), 6.82 (q, 2H), 5.82 (s, 1H), 5.05 (s, 2H), 4.40 (d of d, 1H), 3.18 (d of d, 1H), 2.97 (d of d, 1H); mass spec (70 eV), m/e 217 (M+), 241 (M-O, CH2), 206, 165, 149, 132, 107, 105, 101, 82, 80, 79, 77.

Workup

  1. custom, round bottom flask, fitted with a reflux condenser, a mechanical stirrer/magnetic stirring bar
  2. temperaturethe solution was heated
  3. temperatureat reflux overnight
  4. customcrystallized from the reaction mixture
  5. filtrationwas filtered off
  6. washThe filtrate was washed with aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. customto give the crude product (5.1 g.) which
  10. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8292a00fdffd4023ba98ec02117491b4
Source dataset
uspto-grants-1986_12
Patent number
US04632992

Reaction notes

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