Acetonitrile → HCID 11724607, compound

HRID 868041Notes

Reaction equation

HRID 868041 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-f2c3e514571140178f7e05170fb4a692
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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