Pyridinium chloride → 1-Nitrodibenzothiophen-4-ol

HRID 641197Notes

Reaction equation

HRID 641197 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[C:15]2[S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:14]=2[C:13]([N+:23]([O-:25])=[O:24])=[CH:12][CH:11]=1>O>[N+:23]([C:13]1[C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[S:16][C:15]=2[C:10]([OH:9])=[CH:11][CH:12]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 122571114-Methoxy-1-nitrodibenzo[b,d]thiophene

Product 1

HCID 498570851-Nitrodibenzothiophen-4-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

Solid pyridine hydrochloride (1 kg, 8.7 mol) was added to 4-methoxy-1-nitro-dibenzothiophene (iii)(35.44 g, 187 mmol) and the reaction mixed well before heating to 165° C. with continuous stirring. The mixture was maintained like this for 8 hrs, cooled, diluted with water (500 ml) and extracted into dichloromethane (3×200 ml). 3M sodium hydroxide solution was added to the organic extract until a dark solid precipitated from the solution. The filtrate was removed and the liquor acidified to pH1 using concentrated HCl. The resulting bright yellow solid that formed on acidification was then removed by filtration, washed with water and dried to give the title compound that was suitably pure to be used without any further purification. (35.44 g, 77%) m/z (LC-MS, ESP), RT=3.69 min, (M+H)=246.2, (M−H)=244.1.

Workup

  1. additionthe reaction mixed well
  2. temperatureThe mixture was maintained like this for 8 hrs
  3. temperaturecooled
  4. extractionextracted into dichloromethane (3×200 ml)
  5. addition3M sodium hydroxide solution was added to the
  6. extractionorganic extract until a dark solid
  7. customprecipitated from the solution
  8. customThe filtrate was removed
  9. customThe resulting bright yellow solid that formed on acidification
  10. customwas then removed by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-daf790d3b4f646b1b413c4b349e98a39
Source dataset
uspto-grants-2010_04
Patent number
US07696203B2

Reaction notes

Loading…