Water → HCID 22506827, compound

HRID 985586Notes

Reaction equation

HRID 985586 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([O:10][CH3:11])=[C:5]([CH:12]=[C:13]([N+:15]([O-])=O)[CH3:14])[C:4]=1[CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.C(OCC)(=O)C>[CH3:11][O:10][C:6]1[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:18])[C:5]=1[CH2:12][CH:13]([NH2:15])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 73979924HCID 73979924, compound

Product 1

HCID 22506827HCID 22506827, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,4-dimethoxy-2,5-dimethyl-3-(2-nitro-1-propenyl)benzene (5.0 g, 19.9 mmol) in tetrahydrofuran (100 ml) was added lithium aluminum hydride (4.0 g, 105.4 mmol) with cooling on ice, and the reaction mixture was heated under reflux for 6 hours. To the reaction mixture was added HIFLO-SUPERCEL (trade name) (5 g), and then water was added dropwise (1.5 ml) with cooling on ice. The resultant mixture was suspended in ethyl acetate, filtered and concentrated under reduced pressure to obtain 4.2 g of the desired product as an oil.

Workup

  1. temperaturewith cooling on ice
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 6 hours
  4. additionTo the reaction mixture was added HIFLO-SUPERCEL (trade name) (5 g)
  5. temperaturewith cooling on ice
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5601bf8ffee42c4afe2c04fc9903020
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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