Sodium Hydroxide → 5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 561094Notes

Reaction equation

HRID 561094 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([O:20]CC)=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[OH-].[Na+]>>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 14127986Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 77%

Procedure

A solution of 6 (1.85 g, 5.7 mmol) in a mixture of AcOH—H2O—H2SO4 (8:6:1 v/v, 75 mL) was heated at reflux for 2 h. The reaction mixture was poured into ice water and adjusted to pH 4 with 1M NaOH solution. A precipitate formed and was collected by filtration, washed successively with water and ethanol and then dried to give 7 (1.3 g, 77%) as a light yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customA precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed successively with water and ethanol
  6. customdried

Sources & evidence

ORD record
ord-8136ff04c59840e2b31b05552b340087
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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