Water → 3-amino-N-{3-[(2-chloro-5-methoxyphenyl)amino]quinoxalin-2-yl}benzenesulfonamide hydrochloride

HRID 1050936Notes

Reaction equation

HRID 1050936 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11]1[C:12]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-])=O)[CH:26]=2)(=[O:24])=[O:23])=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.C1COCC1.O.C([O-])=O.[K+]>[Pt]=S.CO.C(O)C>[ClH:1].[NH2:31][C:27]1[CH:26]=[C:25]([S:22]([NH:21][C:12]2[C:11]([NH:10][C:3]3[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=3[Cl:1])=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)(=[O:24])=[O:23])[CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 2735122Potassium FormateHCID 57448456N-(3-((2-chloro-5-methoxyphenyl)amino)quinoxalin-2-yl)-3-nitrobenzenesulfonamide

Product 1

HCID 894999603-amino-N-{3-[(2-chloro-5-methoxyphenyl)amino]quinoxalin-2-yl}benzenesulfonamide hydrochloride

Reagents, catalysts & solvents 3

HCID 82861Platinum sulfide (PtS)CatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 1 kg of N-{3-[(2-chloro-5-methoxyphenyl)amino]quinoxalin-2-yl}-3-nitrobenzenesulfonamide, add a catalytic amount of platinum sulfide on carbon (Pt(S)C), 6 volumes of THF, 0.16 volume of water and 2 volumes of ethanol. The reaction mixture is stirred and heated to reflux. An aqueous potassium formate solution (1.4 volume of water+0.69 kg of potassium formate) is added. The reaction mixture is stirred at reflux until completion of the reaction and cooled down at 50° C. After the addition of 10 volumes of methanol and a one hour stirring, the catalyst is filtered off and washed with 3.4 volumes of methanol. The filtered solution is cooled down at 20° C. 0.62 kg of HCl are added. The reaction mixture is stirred at 20° C., cooled down at 5° C. and filtered. The cake is washed with methanol (6 volumes) and dried under vacuum.

Workup

  1. temperatureheated to reflux
  2. stirringThe reaction mixture is stirred
  3. temperatureat reflux until completion of the reaction
  4. stirringa one hour stirring
  5. filtrationthe catalyst is filtered off
  6. washwashed with 3.4 volumes of methanol
  7. temperatureThe filtered solution is cooled down at 20° C
  8. addition0.62 kg of HCl are added
  9. stirringThe reaction mixture is stirred at 20° C.
  10. temperaturecooled down at 5° C.
  11. filtrationfiltered
  12. washThe cake is washed with methanol (6 volumes)
  13. customdried under vacuum

Sources & evidence

ORD record
ord-c042f6264caf4d778353848d90b31c9a
Source dataset
uspto-grants-2016_07
Patent number
US09388143B2

Reaction notes

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