(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzene → 2-(4-Benzyloxy-phenyl)-ethylamine

HRID 710383

Reaction equation

HRID 710383 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[N+:17]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][NH2:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5702926(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 2009572-(4-Benzyloxy-phenyl)-ethylamineYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the product of Step B (1.06 g; 4.15 mmol) in anhydrous THF (20 ml) was added drop wise to a suspension of LiAlH4 (0.52 g; 13.7 mmol) in anhydrous THF (10 ml) over a period of 1 h at room temperature with vigorous stirring. After additional stirring for 2 h, the reaction mixture was quenched with H2O (1 ml), followed by 10% NaOH (2 ml) and H2O (1 ml). This was stirred for additional 30 min and precipitate formed was filtered off, washed with CH2Cl2 (3×20 ml) and combined filtrates were evaporated to dryness to give the crude title compound (0.71 g; 75%), as a creamy foam, which was used in the next step without further purification. 1H-NMR (CDCl3) 1.5 (broad s, 2H+H2O); 2.71 (tr, 2H, J=6.8 Hz); 2.94 (tr, 2H, J=6.8 Hz); 5.04 (s, 2H); 6.17-6.84 (m, 3H); 7.17-7.43 (m, 6H).

Workup

  1. customthe reaction mixture was quenched with H2O (1 ml)
  2. stirringThis was stirred for additional 30 min
  3. customprecipitate formed
  4. filtrationwas filtered off
  5. washwashed with CH2Cl2 (3×20 ml)
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-bc08079d4e0a4fb9af5a744c01ebad07
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Linked notes

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