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

HRID 1579443Notes

Reaction equation

HRID 1579443 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(Cl)(Cl)(Cl)Cl>O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[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

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 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 962WaterSolvent

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 filtered rapidly while it is hot. The crystals thus obtained are suspended in hot water (about 60°C). The suspension is stirred thoroughly, and filtered. 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 filtered rapidly while it
  3. customThe crystals thus obtained
  4. stirringThe suspension is stirred thoroughly
  5. filtrationfiltered
  6. customThe crystals are recrystallized from dioxane

Sources & evidence

ORD record
ord-4304fc61f292405c8d0dd88cc0977840
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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