Ethanol → 4-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamide

HRID 387851Notes

Reaction equation

HRID 387851 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([S:13][C:14]3[S:15][C:16]([N+:19]([O-])=O)=[CH:17][CH:18]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[C:22]([NH2:24])=[O:23].[Cl-].[NH4+].C(O)C.O>[Fe].CO.C(OCC)(=O)C.CN(C)C=O>[NH2:19][C:16]1[S:15][C:14]([S:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([C:22]([NH2:24])=[O:23])[CH:5]=3)[N:10]=[CH:9][CH:8]=2)=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 229366247-Methoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline-6-carboxamide

Product 1

HCID 229362694-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamideYield 56%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

After suspending 7-methoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline-6-carboxamide (320 mg, 0.885 mmol), iron (247 mg, 4.43 mmol) and ammonium chloride (481 mg, 8.85 mmol) in an ethanol (8 ml)-water (2 ml)-dimethylformamide (1 ml) mixed solvent, the suspension was heated and stirred at 80° C. for 15 minutes. After completion of the reaction, the reaction mixture was filtered with celite and washed in a tetrahydrofuran-methanol mixed solvent. After adding ethyl acetate to the organic layer, it was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:methanol=20:1), and the fraction containing the target substance was concentrated to obtain the title compound (164 mg, 0.495 mmol, 56%) as yellowish-brown crystals.

Workup

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in a tetrahydrofuran-methanol mixed solvent
  6. additionAfter adding ethyl acetate to the organic layer, it
  7. washwas washed with water and saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationthe drying agent was filtered off
  10. distillationthe filtrate was distilled off under reduced pressure
  11. customThe obtained crude product
  12. additionthe fraction containing the target substance
  13. concentrationwas concentrated

Sources & evidence

ORD record
ord-22a3654e9582409d90347fed788c1c57
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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