Pyrrolidine → HCID 13377183, compound

HRID 1981903Notes

Reaction equation

HRID 1981903 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]2[CH2:14][CH:15]([CH3:16])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6]3.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>CN1CCCC1=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:9]2[CH2:14][CH:15]([CH3:16])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6]3

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 133771777-Amino-8,9-difluoro-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

Product 1

HCID 13377183HCID 13377183, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7-Amino-8,9-difluoro-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (0.5 g) and pyrrolidine (0.7 g) are suspended in N-methylpyrrolidone (10 ml), and the mixture is heated at 110°-120° C. for 5 hours in a sealed tube. The reaction mixture is concentrated to dryness under reduced pressure, and to the residue is added ethyl acetate. The resulting crystals are separated by filtration and recrystallized from N,N-dimethylformamide to give 7-amino-8-fluoro-2-methyl-6-oxo-9-(1-pyrrolidinyl)-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (0.2 g) as yellow cubic crystals. m.p. 296°-299° C. (decomp.)

Workup

  1. temperaturethe mixture is heated at 110°-120° C. for 5 hours in a sealed tube
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. additionto the residue is added ethyl acetate
  4. customThe resulting crystals are separated by filtration
  5. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-d9fccccd844d47f0a9a58ff7b5342315
Source dataset
uspto-grants-1986_06
Patent number
US04594347

Reaction notes

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