Furo[3,4-b]quinoline-1,3-dione → 2-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]-3-quinolinecarboxylic acid

HRID 542274

Reaktionsgleichung

Reaktionsgleichung von HRID 542274
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]2[C:11]([O:13][C:14](=[O:15])[C:2]=12)=[O:12].[NH2:16][C:17]([CH3:24])([CH:21]([CH3:23])[CH3:22])[C:18]([NH2:20])=[O:19]>O1CCCC1>[C:18]([C:17]([NH:16][C:14]([C:2]1[C:3]([C:11]([OH:13])=[O:12])=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)=[O:15])([CH3:24])[CH:21]([CH3:23])[CH3:22])(=[O:19])[NH2:20]

Komponenten

4

Edukt 2

HCID 4325463Furo[3,4-b]quinoline-1,3-dioneHCID 97937732-Amino-2,3-dimethylbutanamide

Produkt 1

HCID 134747362-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]-3-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2,3-quinolinedicarboxylic anhydride (0.037 mol) in tetrahydrofuran (THF, 250 mL) is stirred at 5° C. under a drying tube, and a solution of 2-amino-2,3-dimethylbutyramide (0.037 mol) in THF (50 mL) added thereto, in small increments, over a 15 minute period. The reaction mixture is allowed to warm slowly to room temperature for an extended period of time, i.e. about 17 hours. The solvent is evaporated in vacuo to afford a gummy residue, which is triturated with hot ethyl acetate (400 mL) and then filtered to afford the desired 2-[(1-carbamoyl-1,2-dimethylpropyl)-carbamoyl]-3-quinolinecarboxylic acid, mp 172.5°-173.5° C.

Aufarbeitung

  1. customThe solvent is evaporated in vacuo
  2. customto afford a gummy residue, which
  3. customis triturated with hot ethyl acetate (400 mL)
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-64fe55d68e0c4ce7b0d679c2af879df9
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04656283

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