Triethylamine → 4-Quinolone-3-carboxylic acid

HRID 620889Notes

Reaction equation

HRID 620889 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-c079e3ea575b497baa32fd05447e29f9
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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