Ethyl Acetate → 4-[3-(7-Bromo-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

HRID 1721178Notes

Reaction equation

HRID 1721178 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=3)[NH2:17])=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].N[C:24]1C=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1.ClC[C:33]1[CH:42]=CC2C(=CC(Br)=CC=2)N=1.[C:44]([O:47]CC)(=[O:46])C>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([NH:17][C:26](=[O:30])[CH2:27][C:28]([CH2:29][CH3:24])([CH2:42][CH3:33])[C:44]([OH:47])=[O:46])[CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 115683-AminophenolHCID 24758Sodium hydrideHCID 224169157-Bromo-2-(chloromethyl)quinolineHCID 224169203-(7-Bromo-2-quinolinylmethoxy)aniline

Product 1

HCID 224168794-[3-(7-Bromo-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(7-bromo-2-quinolinylmethoxy)aniline: 0.32 g of NaH (95%) is added at 0° to a solution of 1.38 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-7-bromo-quinoline in solid form are then added thereto 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 are combined and concentrated by evaporation to give the title compound which is further purified by crystallisation from CH2Cl2 /ether/hexane.

Workup

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

Sources & evidence

ORD record
ord-4a3012371141420d9b0a407a16e1fab2
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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