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

HRID 1905469Notes

Reaction equation

HRID 1905469 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 (0.037 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.

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-618b2db1861f45439961466f70ce0391
Source dataset
uspto-grants-1989_06
Patent number
US04843162

Reaction notes

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