Water → 2-(2-Bromo-3-cyclopropylmethoxy-phenyl)-ethylamine

HRID 523997Notes

Reaction equation

HRID 523997 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[C:13]([CH:14]=[CH:15][N+:16]([O-])=O)=[CH:12][CH:11]=[CH:10][C:9]=1[O:19][CH2:20][CH:21]1[CH2:23][CH2:22]1.O.[OH-].[Na+]>C1COCC1>[Br:7][C:8]1[C:9]([O:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)=[CH:10][CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][NH2:16]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 1317355752-Bromo-1-cyclopropylmethoxy-3-(2-nitro-vinyl)-benzene

Product 1

HCID 840613812-(2-Bromo-3-cyclopropylmethoxy-phenyl)-ethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 0.92 mL (2.2 mmol) lithium aluminum hydride solution (2.4 M in THF) are added dropwise 300 mg (1.01 mmol) 2-bromo-1-cyclopropylmethoxy-3-(2-nitro-vinyl)-benzene (example XX) in 5 mL THF at 0° C. After stirring at 0° C. for 2 h the reaction mixture is quenched by the addition of 36 μL (2.0 mmol) water, 0.50 mL (2.0 mmol) aq. NaOH solution (c=4 mol/L) and 0.11 mL (6.0 mmol) water. The resulting mixture is stirred for 20 min, filtered over celite/Na2SO4 and the filtrate is concentrated by evaporation. The residue is purified by HPLC (ACN/H2O/NH4OH).

Workup

  1. stirringThe resulting mixture is stirred for 20 min
  2. filtrationfiltered over celite/Na2SO4
  3. concentrationthe filtrate is concentrated by evaporation
  4. customThe residue is purified by HPLC (ACN/H2O/NH4OH)

Sources & evidence

ORD record
ord-2b50f610bc5945bbb23f2f63ddd56a8f
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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