Ethyl Acetate → 4-[3-(7-Acetyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid
Reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH2:14][O:15][C:16]3[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=3)[NH2:19])=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].N[C:26]1C=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1.Cl[CH2:34][C:35]1C=CC2C(=CC(C(=O)C)=CC=2)N=1.[C:48]([O:51]CC)(=[O:50])C>CN(C=O)C>[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH2:14][O:15][C:16]3[CH:17]=[C:18]([NH:19][C:28](=[O:32])[CH2:29][C:30]([CH2:31][CH3:26])([CH2:34][CH3:35])[C:48]([OH:51])=[O:50])[CH:20]=[CH:21][CH:22]=3)=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(7-acetyl-2-quinolinylmethoxy)aniline: 30 mg of NaH (95%) are added at 0° to a solution of 0.13 g of 3-aminophenol in 2.5 ml of DMF and then the batch is stirred for 30 min. at 0°. 0.25 g of 2-chloromethyl-7-acetyl-quinoline in solid form is then added and the batch is stirred for a further one hour at 0° and for another hour at 20°. It is then diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated by evaporation. The evaporation residue is chromatographed on 25 g of silica gel. The product-containing fractions eluted with toluene/ethyl acetate 85:15 are combined and concentrated by evaporation to give the title compound which is further reacted directly.
Workup
- stirringthe batch is stirred for a further one hour at 0° and for another hour at 20°
- washwashed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated by evaporation
- customThe evaporation residue is chromatographed on 25 g of silica gel
- washThe product-containing fractions eluted with toluene/ethyl acetate 85:15
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-7fd1b0716a154950adb94f29f3060f37
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05508408
Reaction notes
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