Methanol → HCID 11725323, compound

HRID 1534467Notes

Reaction equation

HRID 1534467 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][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:24]=[O:25])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:26][Mg]I.CO>ClCCl.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][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:24]([OH:25])[CH3:26])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 103821023-Butyryl-4-(o-tolylamino)quinoline-8-carbaldehydeHCID 178418373HCID 178418373, compound

Product 1

HCID 11725323HCID 11725323, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-butyryl-4-(2-methylphenylamino)-quinoline-8-carbaldehyde (2.0 g, 6 mmol) in dichloromethane (100 ml) was stirred at 0° C. -5° C. and treated with a solution of methylmagnesium iodide in ether until T.L.C. (2% methanol in dichloromethane) showed that mostly new product had formed. The mixture was washed with ammonium chloride solution, dried and evaporated. Chromatography (silica gel, 0.5% methanol in dichloromethane) afforded the required 3-butyryl-4-(2-methylphenylamino)-8-(1-hydroxyethyl)quinoline (0.28 g) as yellow crystals, m.p. 140° C.-2° C.

Workup

  1. customhad formed
  2. washThe mixture was washed with ammonium chloride solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-30fcaee40e574d8ca3dde792531d386d
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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