Pyridine → Dec-3,9-diene

HRID 2163223Notes

Reaction equation

HRID 2163223 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2OC(=O)N[C:6]=2[CH:11]=1.N1C=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[CH3:16][CH2:15][CH:14]=[CH:13][CH2:11][CH2:6][CH2:5][CH2:4][CH:3]=[CH2:2]

Participants

4

Reactant 2

HCID 1049PyridineHCID 268565-Amino-2,3-dihydro-1,3-benzoxazol-2-one

Product 1

HCID 20981468Dec-3,9-diene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of anti-tricyclo[4.2.2.02,5 ]dec-3,9-diene-endo-7,endo-8-dicarboxylic anhydride (2.02 g., 0.01 mole), 5-aminobenzoxazolin-2-one (1.50 g., 0.01 mole) and pyridine (20 ml.) is heated under reflux for six hours. The cooled solution (25° C.) is diluted with water (200 ml.) and the precipitate is collected by filtration, 2.60 g., m.p. 252°-257° C. Recrystallization from 2-propanol provides N-(5-benzoxazolinyl-2-one)-antitricyclo[4.2.2.02,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide, m.p. 287.5°-290° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for six hours
  3. filtrationthe precipitate is collected by filtration, 2.60 g
  4. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-cb7e16574cd940a1be3bd011f72aec14
Source dataset
uspto-grants-1979_01
Patent number
US04132799

Reaction notes

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