Water → 2-(5-Methyl-2-thienyl)ethanamine

HRID 915653Notes

Reaction equation

HRID 915653 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH:7]=[CH:8][N+:9]([O-])=O)=[CH:5][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C>[CH3:1][C:2]1[S:3][C:4]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 539158762-Methyl-5-(2-nitro-vinyl)-thiophene

Product 1

HCID 147881892-(5-Methyl-2-thienyl)ethanamineYield 20.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Add 2-methyl-5-(2-nitrovinyl)thiophene (483 mg crude, 2.855 mmol, 1 eq) as a solution in diethyl ether (15 mL) to a solution of lithium aluminum hydride (227 mg, 5.995 mmol, 2.1 eq) in diethyl ether (5.995 mL) at a rate such as to maintain gentle reflux of the solution. Stir reaction for 5 minutes. Cautiously add water followed by several small portions of potassium sodium tartrate. Stir reaction vigorously for 1 hour and then let stand overnight. Separate organics, dry with magnesium sulfate, and concentrate on rotovap to give 360 mg of crude product as an oil. Perform column chromatography to give 82 mg (20% yield) of 2-(5-methylthiophen-2-yl)ethylamine. MS (m/e): 142.0 (MH+).

Workup

  1. temperatureto maintain gentle
  2. temperaturereflux of the solution
  3. customreaction for 5 minutes
  4. stirringStir
  5. customreaction vigorously for 1 hour
  6. dry with materialSeparate organics, dry with magnesium sulfate
  7. concentrationconcentrate on rotovap
  8. customto give 360 mg of crude product as an oil

Sources & evidence

ORD record
ord-d4000a2965774253ad3b57b539091f4c
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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