Benzo(b)thiophen-3-amine, 2-nitro-N-phenyl- → HCID 86709236, compound

HRID 2174147Notes

Reaction equation

HRID 2174147 reaction equation
[N+:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-])=O>C(O)(=O)C.O.[Fe]>[C:14]1([NH:13][C:5]2[C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[S:8][C:4]=2[NH2:1])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 1

HCID 197891Benzo(b)thiophen-3-amine, 2-nitro-N-phenyl-

Product 1

HCID 86709236HCID 86709236, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Into a solution of 2-nitro-N-phenylbenzo[b]thiophen-3-amine (13 g, 48 mmol) in acetic acid (200 ml) and water (20 ml) was added portionwise iron powder (14 g, 250 mmol). After stirring at room temperature for 2 h, it was filtered through a short plug of Celite and washed with DCM. The combined filtrate was washed with water and aqueous sodium carbonate solution. Upon evaporation off the solvent, the residue was purified by column chromatography on silica gel with hexane/DCM (4/1, v/v) as eluent to yield N3-phenylbenzo[b]thiophene-2,3-diamine (7.5 g, 65%) as a white solid.

Workup

  1. filtrationit was filtered through a short plug of Celite
  2. washwashed with DCM
  3. washThe combined filtrate was washed with water and aqueous sodium carbonate solution
  4. customUpon evaporation off the solvent
  5. customthe residue was purified by column chromatography on silica gel with hexane/DCM (4/1

Sources & evidence

ORD record
ord-f9e2c602194f46479b9f6965b8ea2553
Source dataset
uspto-grants-2015_06
Patent number
US09059412B2

Reaction notes

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