Hydrochloric Acid → HCID 19037079, compound

HRID 264862Notes

Reaction equation

HRID 264862 reaction equation
Br[C:2]1[C:7]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:16][F:17])([CH3:15])[CH:3]=1.Cl.[CH3:19][N:20](C)C=O>>[C:19]([C:2]1[C:7]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH2:16][F:17])([CH3:15])[CH:3]=1)#[N:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 19037032HCID 19037032, compound

Product 1

HCID 19037079HCID 19037079, compound

Procedure

A mixture of 5.6 g of 4-bromo-2-fluoromethyl-2-methyl-6-nitro-2H-1-benzopyran, 1.84 g of cuprous cyanide and 50 ml of N,N-dimethylformamide was refluxed with heating for 5 hours under a nitrogen atmosphere. When aqueous HCl solution was added to the mixture under ice-cooling, crystals were separated out. The crystals were collected by filtration, washed with water and dissolved in methylene chloride. After it washed with water and dried, the solvent was evaporated off. The resultant residue was purified with silica gel column chromatography (developing solution: CH2Cl2) to obtain 3.27 g of 4-cyano-2-fluoromethyl-2-methyl-6-nitro-2H-1-benzopyran with a melting point of 169°-171° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 5 hours under a nitrogen atmosphere
  3. temperaturecooling
  4. customcrystals were separated out
  5. filtrationThe crystals were collected by filtration
  6. washwashed with water
  7. dissolutiondissolved in methylene chloride
  8. washAfter it washed with water
  9. customdried
  10. customthe solvent was evaporated off
  11. customThe resultant residue was purified with silica gel column chromatography (developing solution: CH2Cl2)

Sources & evidence

ORD record
ord-ebf95fe5b926482e81b75568e3519a67
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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