Methanol → 4-(Thiophen-3-yl)aniline

HRID 1665696Notes

Reaction equation

HRID 1665696 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[CH:8][CH:7]=2)=[CH:2]1.[OH-].[Na+].CO>O>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57875827N-(4-thiophen-3-yl-phenyl)-acetamide

Product 1

HCID 41303364-(Thiophen-3-yl)anilineYield 115.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of N-(4-thiophen-3-yl-phenyl)-acetamide (90 mg, 0.41 mmol), NaOH (133 mg, 3.3 mmol), MeOH (2 mL) and water (7 mL) was heated to reflux for 12 hr. After completion of the reaction, the reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine solution and dried over sodium sulphate. The organic layer collected was concentrated under reduced pressure to afford 83 mg (crude) of 4-thiophen-3-yl-phenylamine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hr
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washwashed with brine solution
  6. dry with materialdried over sodium sulphate
  7. customThe organic layer collected
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-bdae6228121d4401b4e8e5c5a55bf135
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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