Acetonitrile → HCID 11724607, compound

HRID 978499Notes

Reaction equation

HRID 978499 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]([N:22](CC)[CH2:23][CH3:24])[CH3:21].C(#[N:29])C>>[NH2:29][CH:21]1[CH2:24][CH2:23][N:22]([C:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:15])[CH2:20]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 11724607HCID 11724607, compound

Conditions

Temperature
5 °C

Procedure

A suspension of 0.81 g (3.0 mmole) of 1-ethyl-1,4-dihydro-6,7,8-trifluoro-4-oxo-3-quinolinecarboxylic acid, 1.28 g (10 mmole) of 3-acetylamminopyrrolidine [U.S. Pat. No. 4,341,784] and 1.5 g (15 mmole) of triethylamine in 50 ml of acetonitrile was refluxed for four hours. The solvent was removed in vacuo and the residue was dissolved in 50 ml of 6.0M hydrochloric acid/ethanol (1:1). The mixture was refluxed for four hours and the ethanol was removed in vacuo. The residue was diluted to 100 ml with water and adjusted to pH 7.3 with 1.0N sodium hydroxide. After cooling to 5° C., the precipitate was removed by filtration, washed successively with water, ethanol, ether, and dried in vacuo to give 0.6 g of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 240°-242° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 50 ml of 6.0M hydrochloric acid/ethanol (1:1)
  3. temperatureThe mixture was refluxed for four hours
  4. customthe ethanol was removed in vacuo
  5. additionThe residue was diluted to 100 ml with water
  6. customthe precipitate was removed by filtration
  7. washwashed successively with water, ethanol, ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-596c1512e2d9471181617a0862354cf2
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

Loading…