2-Nitro-4-(thiophen-2-yl)aniline → 4-(Thiophen-2-yl)benzene-1,2-diamine

HRID 509184Notes

Reaction equation

HRID 509184 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1.[H][H]>[Pd]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:10])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 226648312-Nitro-4-(thiophen-2-yl)anilineHCID 178418361HCID 178418361, compound

Product 1

HCID 130078054-(Thiophen-2-yl)benzene-1,2-diamineYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 4-thienyl-2-nitroaniline (1 equiv, 400 mg, 1.82 mmol) was added 10% Pd/C (0.05 equiv, 97 mg, 0.09 mmol). The resulting suspension was stirred for overnight over 1 atm of hydrogen. The solids were filtered through celite pad and the filtrate was concentrated under vacuum. The crude material was purified by silica gel column chromatography with gradient of MeOH (0-10%) in CH2Cl2 to afford compound 30 (310 mg, 90%) and a white solid. LRMS (ESI): (calc) 190.2 (found) 191.0 (MH)+.

Workup

  1. filtrationThe solids were filtered through celite pad
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe crude material was purified by silica gel column chromatography with gradient of MeOH (0-10%) in CH2Cl2

Sources & evidence

ORD record
ord-037a3ffdd9f646d0a19cd473696eb089
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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