2-(1-Benzothien-2-yl)-5-nitrobenzamide → 5-Amino-2-(1-benzothien-2-yl)benzamide

HRID 503691Notes

Reaction equation

HRID 503691 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13]>[Pt](=O)=O.C1COCC1>[NH2:19][C:16]1[CH:17]=[CH:18][C:10]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)=[C:11]([CH:15]=1)[C:12]([NH2:14])=[O:13]

Participants

4

Reactant 1

HCID 594284732-(1-Benzothien-2-yl)-5-nitrobenzamide

Product 1

HCID 594284755-Amino-2-(1-benzothien-2-yl)benzamide

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(1-Benzothien-2-yl)-5-nitrobenzamide (4.75 g) is introduced into THF (250 ml) and, after addition of platinum dioxide (0.57 g), hydrogenated at RT under atmospheric pressure overnight. The reaction mixture is filtered through kieselguhr and washed with THF, and the organic phase is concentrated. The residue is stirred with diethyl ether, and the crystals are filtered off with suction. They are washed with diethyl ether and a little DCM and dried. Yield 2.39 g (56% of theory).

Workup

  1. customhydrogenated at RT
  2. customunder atmospheric pressure overnight
  3. filtrationThe reaction mixture is filtered through kieselguhr
  4. washwashed with THF
  5. concentrationthe organic phase is concentrated
  6. filtrationthe crystals are filtered off with suction
  7. washThey are washed with diethyl ether
  8. dry with materiala little DCM and dried

Sources & evidence

ORD record
ord-dae33f6921ab44e191d34584109884bd
Source dataset
uspto-grants-2010_08
Patent number
US07776922B2

Reaction notes

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