1,3-dimethoxy-5-(2-nitroethenyl)benzene → 3,5-Dimethoxyphenethylamine

HRID 2414811Notes

Reaction equation

HRID 2414811 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH:16][N+:17]([O-])=O)[CH:12]=[C:11]([O:20][CH3:21])[CH:10]=1>C1COCC1>[CH3:21][O:20][C:11]1[CH:12]=[C:13]([CH2:15][CH2:16][NH2:17])[CH:14]=[C:9]([O:8][CH3:7])[CH:10]=1

Participants

4

Reactant 2

HCID 6106161,3-dimethoxy-5-(2-nitroethenyl)benzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 1378573,5-Dimethoxyphenethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (1.76 g, 46.4 mmol) in THF (30 mL) is added at 0° C. dropwise a solution of 1,3-dimethoxy-5-(2-nitro-vinyl)-benzene (2.43 g, 11.6 mmol; Gairaud C B, Lappin G R, J Org Chem 1953, 18, 1) in THF (70 mL). The mixture is stirred for 30 min at this temperature and then at reflux for 4 h. The reaction mixture is quenched by the subsequent addition of 2 N NaOH (20 mL) and stirred for another 15 min at ambient temperature. The aqueous solution is extracted three times with EtOAc. The combined organic layers are dried with anhydrous MgSO4, filtered and concentrated to give the title compound as a yellow oil.

Workup

  1. temperatureat reflux for 4 h
  2. customThe reaction mixture is quenched by the subsequent addition of 2 N NaOH (20 mL)
  3. stirringstirred for another 15 min at ambient temperature
  4. extractionThe aqueous solution is extracted three times with EtOAc
  5. dry with materialThe combined organic layers are dried with anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-00d243a718ca42de8673e015501e46a6
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

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