1-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-(3,8-Diazaspiro[4.4]nonan-8-yl)-1-ethyl-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid

HRID 978504Notes

Reaction equation

HRID 978504 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[CH2:20]1[C:24]2([CH2:28][CH2:27][NH:26][CH2:25]2)[CH2:23][CH2:22][NH:21]1>C(#N)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:21]3[CH2:22][CH2:23][C:24]4([CH2:28][CH2:27][NH:26][CH2:25]4)[CH2:20]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 126918832,7-Diaza-spiro[4.4]nonane

Product 1

HCID 4614467-(3,8-Diazaspiro[4.4]nonan-8-yl)-1-ethyl-6,8-difluoro-4-oxo-quinoline-3-carboxylic acidYield 103.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.81 g (3.0 mmol) 1-ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid in 40 ml acetonitrile was treated with 0.80 g (6.3 mmol) 2,7-diazaspiro[4.4]nonane [J. Org. Chem. 46, 2757 (1981)] and the mixture stirred two days at room temperature, refluxed 1.5 hours, cooled, and filtered to afford 1.17 g of the title compound, mp 234°-240° C. (dec).

Workup

  1. temperaturerefluxed 1.5 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-935c20f501e843b7b746537660a7e860
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

Loading…