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

HRID 1721180Notes

Reaction equation

HRID 1721180 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].[CH2:23]([C:25]1([CH2:32][CH3:33])[CH2:30][C:29](=[O:31])[O:28][C:26]1=[O:27])[CH3:24]>N1C=CC=CC=1>[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:29](=[O:31])[CH2:30][C:25]([CH2:32][CH3:33])([CH2:23][CH3:24])[C:26]([OH:28])=[O:27])[CH:20]=[CH:21][CH:22]=3)=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 137741Dihydro-3,3-diethyl-2,5-furandioneHCID 224169223-(7-Acetyl-2-quinolinylmethoxy)aniline

Product 1

HCID 224169144-[3-(7-Acetyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.36 g of 3-(7-acetyl-2-quinolinylmethoxy)aniline and 0.385 g of 2,2-diethylsuccinic acid anhydride are stirred in 5 ml of pyridine for 72 hours at 20° and concentrated by evaporation. The residue is suspended in 5 ml of 2N aqueous hydrochloric acid, the suspension is stirred for 30 min. at 20° and filtered and the residue retained on the filter is dried in vacuo at 20°. The crude product obtained is chromatographed on 50 g of silica gel. The product-containing fractions (eluted with toluene/ethyl acetate 1:1 and with ethyl acetate) are combined and concentrated by evaporation and the evaporation residue is recrystallised from a CH2Cl2 /methanol/acetone mixture to give the title compound in the form of crystals of m.p. 164°. IR (Nujol): inter alia 3600-2100, 3350, 1675, 1600 cm-1.

Workup

  1. concentrationconcentrated by evaporation
  2. filtrationfiltered
  3. customis dried in vacuo at 20°
  4. customThe crude product obtained
  5. customis chromatographed on 50 g of silica gel
  6. washThe product-containing fractions (eluted with toluene/ethyl acetate 1:1 and with ethyl acetate)
  7. concentrationconcentrated by evaporation
  8. customthe evaporation residue is recrystallised from a CH2Cl2 /methanol/acetone mixture

Sources & evidence

ORD record
ord-e324ed444ffc45819a9344aefa5051aa
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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