Triethylamine → 4-Quinolone-3-carboxylic acid

HRID 2372089Notes

Reaction equation

HRID 2372089 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(NCC1CCNC1)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 13491786Ethyl-pyrrolidin-3-ylmethyl-amine

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, 1.93 g (15 mmole) of N-ethyl-3-pyrrolidinemethanamine, 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-(ethylamino)methyl-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-101435aaf05047029df4559fd8340b90
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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