Tetrahydrofuran → 3-Amino-2-[1,1'-biphenyl]-4-yl-6-chloro-4-quinolinecarboxylic acid

HRID 1073258Notes

Reaction equation

HRID 1073258 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-].[Na+].Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=O.[O:32]1CCCC1>O.C(O)C.O>[NH2:16][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:11])=[O:32])=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 872035-chloro-1H-indole-2,3-dione2×HCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

Product 1

HCID 150859523-Amino-2-[1,1'-biphenyl]-4-yl-6-chloro-4-quinolinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

A 3.63 g portion of 5-chloroisatin was added to 35 ml of water in a three-necked, 500 ml flask. A solution of 5.6 g of sodium hydroxide in 20 ml of water was added and the mixture was stirred at 90° C. A solution of 7.43 g of 2-amino-4'-phenylacetophenone hydrochloride in 93 ml of ethanol:water (1:1) was warmed, 25 ml of tetrahydrofuran added to maintain solution and this solution added dropwise to the 5-chloroisatin solution over 3 hours. The solvent was distilled off at 85° C. The remaining solution was cooled, 50 ml of water added and this mixture stirred for 10 minutes. The resulting red solid was collected, dried, stirred in 2.5 liters of water for 1.5 hours and filtered. The filtrate was acidified to pH 4, then the resulting solid was collected, washed with water and dried, giving 5.15 g of the desired product as a yellow solid, mp 244°-245° C.

Workup

  1. temperatureto maintain solution
  2. distillationThe solvent was distilled off at 85° C
  3. temperatureThe remaining solution was cooled
  4. addition50 ml of water added
  5. stirringthis mixture stirred for 10 minutes
  6. customThe resulting red solid was collected
  7. customdried
  8. stirringstirred in 2.5 liters of water for 1.5 hours
  9. filtrationfiltered
  10. customthe resulting solid was collected
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-d4f40d799cbc4c18bcd7fda533adc202
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

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