Ethyl Acetate → 4-[3-(6-Methyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

HRID 1721183Notes

Reaction equation

HRID 1721183 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])[CH:6]=[CH:5]2.[H-].[Na+].N[C:24]1C=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1.ClCC1C=CC2C(=CC=[C:38]([CH3:43])C=2)N=1.[C:44]([O:47]CC)(=[O:46])C>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][O:13][C:14]1[CH:15]=[C:16]([NH:17][C:26](=[O:30])[CH2:27][C:28]([CH2:29][CH3:24])([CH2:38][CH3:43])[C:44]([OH:47])=[O:46])[CH:18]=[CH:19][CH:20]=1)[CH:6]=[CH:5]2

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 115683-AminophenolHCID 24758Sodium hydrideHCID 147504892-(Chloromethyl)-6-methylquinolineHCID 224168803-(6-Methyl-2-quinolinylmethoxy)aniline

Product 1

HCID 224168764-[3-(6-Methyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(6-methyl-2-quinolinylmethoxy)aniline: 0.43 g of NaH (95%) is added at 0° to a solution of 1.85 g of 3-aminophenol in 30 ml of DMF and then the batch is stirred for 30 min. at 0°. 3.2 g of 2-chloromethyl-6-methyl-quinoline [see C.A. 82, 57733p and U.S. Pat. No. 3,829,573] in solid form are 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 250 g of silica gel. The product-containing fractions eluted with toluene/ethyl acetate 95:5 and 9:1 are combined and concentrated by evaporation to give the title compound which is further purified by being crystallised twice from CH2Cl2 /ether/hexane.

Workup

  1. addition3,829,573] in solid form are then added
  2. stirringthe batch is stirred for a further one hour at 0° and for another hour at 20°
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by evaporation
  6. customThe evaporation residue is chromatographed on 250 g of silica gel
  7. washThe product-containing fractions eluted with toluene/ethyl acetate 95:5 and 9:1
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ad93826907d84eeb8f760e2e380edf68
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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