Methane → HCID 19592905, compound

HRID 613470Notes

Reaction equation

HRID 613470 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Se](=O)=[O:16].C.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C.CO.O1CCCC1.C(OCC)C>[OH:16][CH2:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 297MethaneHCID 24007Selenium DioxideHCID 25517Ammonium ChlorideHCID 760484-Methyl-8-nitroquinolineHCID 4311764Sodium borohydride

Product 1

HCID 19592905HCID 19592905, compoundYield 21.9%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methyl-8-nitroquinoline (2.80 g) and selenium(IV) oxide (1.82 g) in ethanol (45 ml) was refluxed for 4 hours. The mixture was treated with active charcoal and filtered through Celite pad. The filtrate was concentrated in vacuo to afford a brown solid. This residue was dissolved in a mixture of methanol (10 ml) and tetrahydrofuran (10 ml) and cooled in an ice bath. To this solution was added sodium borohydride (170 mg) and stirred at the same temperature for half an hour. To this mixture was added saturated ammonium chloride solution and extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by a flash chromatography on silica gel using methylene chloride then 3% methanol in methylene chloride as the eluent to give a solid. This solid was solidified with diethyl ether to afford 4-hydroxymethyl-8-nitroquinoline (665 mg) as a brown solid.

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationfiltered through Celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a brown solid
  5. temperaturecooled in an ice bath
  6. extractionextracted with methylene chloride
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by a flash chromatography on silica gel
  10. custom3% methanol in methylene chloride as the eluent to give a solid

Sources & evidence

ORD record
ord-66b7573bc84c459895366aa5b15bc428
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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