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

HRID 1649875Notes

Reaction equation

HRID 1649875 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,3-quinolinedicarboxylic anhydride (0.37 mol) in tetrahydrofuran (THF, 250 mL) is stirred at 5° C. under a drying tube, and a solution of 2-amino-2,3-dimethylbutyramide (0.37 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.

Workup

  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

Sources & evidence

ORD record
ord-e827c00bc27e4ba08d4231e3fc47766b
Source dataset
uspto-grants-1990_05
Patent number
US04921961

Reaction notes

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