HCID 10450418, compound → HCID 10090183, compound

HRID 1647477Notes

Reaction equation

HRID 1647477 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:25]=[O:26])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:27][Mg]I>O1CCCC1.CCOCC>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:25]([OH:26])[CH3:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 10450418HCID 10450418, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 10090183HCID 10090183, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Butyryl-4-(4-hydroxy-2-methylphenylamino)quinoline-8-carbaldehyde (2.0 g, 6 mmol) was stirred in dry tetrahydrofuran (200 ml) at j-30° C. and treated with a solution of methylmagnesium iodide in ether. Cooling was removed and the mixture was allowed to warm to room temperature. The mixture was washed with saturated ammonium chloride solution (×2) and the aqueous extracted with dichloromethane. The combined organics were dried and evaporated to afford a brown oil which was chromatographed (silica gel, 1% methanol in dichloromethane) to return aldehyde starting material (0.16 g ) and give 3-butyryl-4-(4-hydroxy-2-methyl-phenylamino)-8-(1-hydroxyethyl)quinoline as yellow crystals from ether-petrol (0.45 g, 21.5%), m.p. 182°-4° C.

Workup

  1. temperatureCooling
  2. customwas removed
  3. washThe mixture was washed with saturated ammonium chloride solution (×2)
  4. extractionthe aqueous extracted with dichloromethane
  5. customThe combined organics were dried
  6. customevaporated
  7. customto afford a brown oil which
  8. customwas chromatographed (silica gel, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-57d43b47bf4c4451bad151eaffeec30c
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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