N-bromobutanimide → 5H-[1]Benzopyrano[2,3-b]pyridin-5-one, 7-(bromomethyl)-

HRID 1579375Notes

Reaction equation

HRID 1579375 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[C:7](=[O:15])[C:6]=2[CH:16]=1.[Br:17]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[C:7](=[O:15])[C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 122026795H-[1]Benzopyrano[2,3-b]pyridin-5-one, 7-methyl-

Product 1

HCID 122742035H-[1]Benzopyrano[2,3-b]pyridin-5-one, 7-(bromomethyl)-Yield 81.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 42 g of 7-methyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine, 36 g of N-bromosuccinimide, 0.4 g of benzoyl peroxide and 420 ml of carbon tetrachloride is refluxed with stirring under ultraviolet light for 2 hours. The reaction mixture is quickly filtered while it is hot. The crystals are suspended in hot water (about 60°C), and the suspension is thoroughly stirred and filtered again. The crystals are recrystallized from dioxane to give 47.1 g of 7-bromomethyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine melting at 211°-212.5°C.

Workup

  1. temperatureis refluxed
  2. filtrationThe reaction mixture is quickly filtered while it
  3. customare suspended in hot water (about 60°C)
  4. stirringthe suspension is thoroughly stirred
  5. filtrationfiltered again
  6. customThe crystals are recrystallized from dioxane

Sources & evidence

ORD record
ord-70ee216c99ca4d23a2d8efd4bcbd8aa0
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

Loading…