Aluminium lithium hydride → HCID 53446860, compound

HRID 2419240Notes

Reaction equation

HRID 2419240 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[S:10][C:11]([O:22][CH3:23])=[C:12]([CH3:21])[C:13]=1[CH:14]=[C:15]([N+:18]([O-])=O)[CH2:16][CH3:17]>CCOCC.C1COCC1>[NH2:18][CH:15]([CH2:16][CH3:17])[CH2:14][C:13]1[C:12]([CH3:21])=[C:11]([O:22][CH3:23])[S:10][C:9]=1[O:8][CH3:7]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53446861HCID 53446861, compound

Product 1

HCID 53446860HCID 53446860, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a refluxing mixture of 1.4 g of lithium aluminum hydride in 10 ml of anhydrous ether and 40 ml of dry THF is slowly added 1.8 g of 1-[2,5-dimethoxy-4-methylthiophenyl]-2-nitro-1-butene. An additional 20 ml of THF is added to dissolve and wash all the nitro compound into the THF mixture. Refluxing is continued for seven hours. The mixture is cooled and ice water (3.4 ml) slowly added to decompose the excess lithium aluminum hydride. When the decomposition is complete, the mixture is filtered and the solid cake washed with THF. The filtrate is evaporated in vacuo to produce crude 2-amino-1-(2,5-dimethoxy-4-methylthiophenyl)butane. The crude is purified as the hydrochloride salt by recrystallization from isopropanol.

Workup

  1. dissolutionto dissolve
  2. washwash all the nitro compound into the THF mixture
  3. temperatureRefluxing
  4. temperatureThe mixture is cooled
  5. additionice water (3.4 ml) slowly added
  6. filtrationthe mixture is filtered
  7. washthe solid cake washed with THF
  8. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-9bf8cd755a1248c2aada32386c58d81d
Source dataset
uspto-grants-1978_08
Patent number
US04105695

Reaction notes

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