O-Toluidine → Quinoline

HRID 1534480Notes

Reaction equation

HRID 1534480 reaction equation
C([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2COC(=O)C1C=CC=CC=1)(=O)C(C)C.CC1C=CC=CC=1N>O1CCOCC1>[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 10384366HCID 10384366, compound

Product 1

HCID 7047QuinolineYield 113%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-isobutyryl-4-chloro-8-benzoyloxymethylquinoline (3.68 g, 10 mmol) and 2-methylaniline (2.13 ml, 20 mmol) in dioxan (50 ml) was heated at reflux for 2 hours, then evaporated, taken up in dichloromethane, washed with aqueous sodium bicarbonate, water and brine, dried and evaporated to an oil. This was taken up in 1% methanolic sodium hydroxide solution (100 ml) and stirred vigorously for 1 hour. The methanol was evaporated, water and dichloromethane added, the aqueous phase adjusted to pH 10 and extracted with dichloromethane. The organic extracts were dried, evaporated and chromatographed (silica, gel, 1%-2% methanol in dichloromethane). Trituration of the product fractions with ether followed by recrystallization from aqueous methanol gave 3-isobutyryl-4-(2-methylphenylamino)-8-hydroxymethyl)quinoline (1.46 g, 44%), m.p. 116°-118°.

Workup

  1. temperatureat reflux for 2 hours
  2. customevaporated
  3. washwashed with aqueous sodium bicarbonate, water and brine
  4. customdried
  5. customevaporated to an oil
  6. customThe methanol was evaporated
  7. additionwater and dichloromethane added
  8. extractionextracted with dichloromethane
  9. customThe organic extracts were dried
  10. customevaporated
  11. customchromatographed (silica, gel, 1%-2% methanol in dichloromethane)
  12. customTrituration of the product fractions with ether followed by recrystallization from aqueous methanol

Sources & evidence

ORD record
ord-01912ff5ffe342eda9c9505db63865b4
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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