Pyridine → HCID 19895591, compound

HRID 892531Notes

Reaction equation

HRID 892531 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[O:3]1.N1C=CC=CC=1.[Cl:25]Cl>C(Cl)(Cl)(Cl)Cl>[Cl:25][C:15]1[CH:16]=[CH:17][C:4]2[O:3][C:2]([CH3:18])([CH3:1])[CH2:7][CH:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[C:5]=2[CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24526ChlorineHCID 198956113,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran

Product 1

HCID 19895591HCID 19895591, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

1 g of 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran was dissolved in 20 ml of carbon tetrachloride at room temperature and 0.25 ml of pyridine and 10 ml of a 0.42M solution of chlorine in carbon tetrachloride were added. After 30 minutes the mixture was washed with sodium bicarbonate solution, the organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 1% (v/v) methanol/dichloromethane and then 2% (v/v) methanol/dichloromethane for the elution. The product was recrystallized from t-butyl methyl ether to give 200 mg of 6-chloro-3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran of melting point 124°-125° C.

Workup

  1. washAfter 30 minutes the mixture was washed with sodium bicarbonate solution
  2. customthe organic phase was separated
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel using 1% (v/v) methanol/dichloromethane
  6. wash2% (v/v) methanol/dichloromethane for the elution
  7. customThe product was recrystallized from t-butyl methyl ether

Sources & evidence

ORD record
ord-f84086ecfb194aa5a6804c13fa3e1431
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

Loading…