Triethylamine → 3-amino-4-(2-chlorophenyl)-1,6,7-trimethyl-2(1H)-quinolone

HRID 1588741Notes

Reaction equation

HRID 1588741 reaction equation
C([N:3](CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:24]2[C:19](=[CH:20][C:21]([CH3:26])=[C:22]([CH3:25])[CH:23]=2)[N:18]([CH3:27])[C:17](=[O:28])[C:16]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C1C=CC=CC=1>[NH2:3][C:16]1[C:17](=[O:28])[N:18]([CH3:27])[C:19]2[C:24]([C:15]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[Cl:8])=[CH:23][C:22]([CH3:25])=[C:21]([CH3:26])[CH:20]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 10359990HCID 10359990, compound

Product 1

HCID 197544703-amino-4-(2-chlorophenyl)-1,6,7-trimethyl-2(1H)-quinoloneYield 69.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Triethylamine (0.7 ml) was added dropwise to a mixture of 4-(2-chlorophenyl)-1,2-dihydro-1,6,7-trimethyl-2-oxo-3-quinolinecarboxylic acid (1.71 g), diphenylphosphoryl azide (1.65 g) and benzene (25 ml) under stirring. The mixture was further stirred for 15 minutes at room temperature and for 30 minutes under reflux, and then distilled to remove the solvent. The residue was dissolved in a mixture of dioxane (20 ml) and 1sodium hydroxide (7.5 ml) , followed by refluxing for 15 minutes. The resulting solution was acidified with 2N hydrochloric acid and then stirred for 20 minutes at room temperature. The mixture was made alkaline with 2N sodium hydroxide. The resultant crystals were collected by filtration to give 3-amino-4-(2-chlorophenyl)-1,6,7-trimethyl-2(1H)-quinolone (1.08 g, 69.2%), which was recrystallized from a mixture of chloroform and ethanol to give colorless needles. mp 242°-243° C.

Workup

  1. stirringThe mixture was further stirred for 15 minutes at room temperature and for 30 minutes
  2. temperatureunder reflux
  3. distillationdistilled
  4. customto remove the solvent
  5. dissolutionThe residue was dissolved in a mixture of dioxane (20 ml) and 1sodium hydroxide (7.5 ml)
  6. temperatureby refluxing for 15 minutes
  7. stirringstirred for 20 minutes at room temperature
  8. filtrationThe resultant crystals were collected by filtration

Sources & evidence

ORD record
ord-ff5bebcbe2524b6a859425d2d640a398
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

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