Acetonitrile → HCID 11724607, compound

HRID 622481Notes

Reaction equation

HRID 622481 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-94f61d07b77d4d46aa90cdb2c1f5b5c1
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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