HCID 10450418, compound → HCID 10090183, compound

HRID 1534492Notes

Reaction equation

HRID 1534492 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 -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 (x2) 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-methylphenylamino)-8-(1-hydroxyethyl)quinoline as yellow crystals from ether-petrol (0.45 g, 21.5%), m.p. 182° C.-4° C.

Workup

  1. temperatureCooling
  2. customwas removed
  3. washThe mixture was washed with saturated ammonium chloride solution (x2)
  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-050ec2940aa44244b12b9579a9e93c89
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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