Dihydro-3,3-diethyl-2,5-furandione → 4-[3-(6-Methyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

HRID 1721182Notes

Reaction equation

HRID 1721182 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.[CH2:21]([C:23]1([CH2:30][CH3:31])[CH2:28][C:27](=[O:29])[O:26][C:24]1=[O:25])[CH3:22]>N1C=CC=CC=1>[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:27](=[O:29])[CH2:28][C:23]([CH2:30][CH3:31])([CH2:21][CH3:22])[C:24]([OH:26])=[O:25])[CH:18]=[CH:19][CH:20]=1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 137741Dihydro-3,3-diethyl-2,5-furandioneHCID 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 1049PyridineSolvent

Procedure

2.05 g of 3-(6-methyl-2-quinolinylmethoxy)aniline and 2.42 g of 2,2-diethylsuccinic acid anhydride are stirred in 30 ml of pyridine for 72 hours at 20° and concentrated by evaporation. The residue is suspended in 25 ml of 2N aqueous hydrochloric acid and the suspension is stirred for 30 min. at 20° and filtered. The precipitate is washed with water and crystallised from ethanol to give the title compound in the form of crystals of m.p. 175°, IR (Nujol): inter alia 3600-2600, 3320, 1685, 1545 cm-1.

Workup

  1. concentrationconcentrated by evaporation
  2. filtrationfiltered
  3. washThe precipitate is washed with water
  4. customcrystallised from ethanol

Sources & evidence

ORD record
ord-00680916552e4589bb94e57d22a382d1
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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