2,4-Dimethoxybenzylamine → HCID 19421429, compound

HRID 744020Notes

Reaction equation

HRID 744020 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](OC)=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1.[CH3:17][O:18][C:19]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22]>O1CCCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:22][CH2:21][C:20]2[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:19]=2[O:18][CH3:17])=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 13806181HCID 13806181, compound

Product 1

HCID 19421429HCID 19421429, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-1-methoxy-2-nitronaphthalene (3,5 g, 12.5 mmol) in dry tetrahydrofuran (15 ml) was dropwise added 2,4-dimethoxybenzylamine (8,5 g, 41,6 mmol) in dry tetrahydrofuran (15 ml). The mixture was stirred at room temperature overnight and evaporated to dryness. The residue was submitted to flash chromatography (SiO2) eluting with toluene/ethyl acetate (1:1). The product was taken up in ethyl acetate and precipitated with light petroleum to give 4.1 g (78%) of the title compound. M.p. 104°-105° C.

Workup

  1. customevaporated to dryness
  2. washeluting with toluene/ethyl acetate (1:1)
  3. customprecipitated with light petroleum

Sources & evidence

ORD record
ord-84b5e79c9a434d0d9d97608e8f7de6ec
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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