Sodium Hydroxide → HCID 19940137, compound

HRID 1493520Notes

Reaction equation

HRID 1493520 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:10]=[C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[NH:8][C:7]=1[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)([O-])=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.O>[OH-:2].[NH4+:1].[NH2:1][CH2:4][CH2:5][C:6]1[CH:10]=[C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[NH:8][C:7]=1[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 54574080HCID 54574080, compound

Product 2

HCID 14923Ammonium HydroxideHCID 19940137HCID 19940137, compoundYield 130.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of crude 3-(2'-nitrovinyl)-2,5-dithienylpyrrole (127 mg) in pure dry tetrahydrofuran (1.5 mL) was added with stirring to a suspension of lithium aluminum hydride (47 mg, 1.23 mmol) in boiling tetrahydrofuran (2 mL) at a rate sufficient to maintain reflux. The mixture was refluxed for 35 minutes, then cooled, and the excess of hydride decomposed by successive addition of 50 μL of H2O, 50 μL of 40% aqueous sodium hydroxide solution and 150 μL of water. The reaction mixture was allowed to stir at room temperature for one hour. The resultant suspension was then filtered through a pad of anhydrous magnesium sulfate and the filter cake washed four times with ethyl acetate (50 mL). The combined filtrate was evaporated under reduced pressure, leaving a straw-colored solid. This solid was then purified on 50 g of silica gel. Elution with methanol: chloroform:ammonium hydroxide, 1:20:0.1, gave 75 mg (82%, 2 steps) of 3-aminoethyl-2,5-dithienyl pyrrole.

Workup

  1. temperatureto maintain
  2. temperaturereflux
  3. temperatureThe mixture was refluxed for 35 minutes
  4. temperaturecooled
  5. filtrationThe resultant suspension was then filtered through a pad of anhydrous magnesium sulfate
  6. washthe filter cake washed four times with ethyl acetate (50 mL)
  7. customThe combined filtrate was evaporated under reduced pressure
  8. customleaving a straw-colored solid
  9. customThis solid was then purified on 50 g of silica gel
  10. washElution with methanol

Sources & evidence

ORD record
ord-7a580f358cba400ea4a12b93c2563d42
Source dataset
uspto-grants-1991_06
Patent number
US05021586

Reaction notes

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