Dihydro-3,3-diethyl-2,5-furandione → 4-[3-(7-Bromo-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

HRID 1721177Notes

Reaction equation

HRID 1721177 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.[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>[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: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]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

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

Procedure

2 g of 3-(7-bromo-2-quinolinylmethoxy)aniline and 1.9 g of 2,2-diethylsuccinic acid anhydride (purified by distillation) are stirred in 28 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 colourless crystals of m.p. 175°, IR (Nujol): inter alia 3600-2100, 3308, 1710, 1670, 1610, 1600, 1497 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-438314f2cf1c4edd97cb2c4a6dab684f
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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