Triethylamine → 4-Quinolone-3-carboxylic acid

HRID 620887Notes

Reaction equation

HRID 620887 reaction equation
C([N:3]1[C:12]2[C:7](=[C:8](N)[C:9](F)=[C:10](F)[C:11]=2F)[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)C.C(OC(NC1CCNC1)=O)(C)(C)C.C(N(CC)CC)C>C(#N)C>[O:17]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:3][CH:4]=[C:5]1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1508834HCID 1508834, compoundHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 2208754-Quinolone-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3.02 g (10 mmole) of 1-ethyl-5-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro quinoline-3-carboxylic acid, 2.79 g (15 mmole) of 3-(t-butoxycarbonylamino)pyrrolidine, 3.0 g (30 mmole) of triethylamine and 100 ml of acetonitrile is refluxed for 18 hours. The reaction mixture is cooled to room temperature and the precipitate is removed by filtration, washed with acetonitrile, ether, and dried in vacuo to give 1-ethyl-5-amino-6,8-difluoro-7-[3-(t-butoxycarbonylamino)-1-pyrrolidinyl[-4-oxo-1,4-dihydroquinoline-3-carboxylic acid.

Workup

  1. temperatureis refluxed for 18 hours
  2. customthe precipitate is removed by filtration
  3. washwashed with acetonitrile, ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-fc3b050b6acf4b52a8e3888a127e5835
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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