HCID 19093016, compound → HCID 19092984, compound

HRID 487732Notes

Reaction equation

HRID 487732 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[CH:8][C:7]=1[N+:18]([O-])=O>C(O)C.[Pd]>[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[CH:8][C:7]=1[NH2:18]

Participants

4

Reactant 1

HCID 19093016HCID 19093016, compound

Product 1

HCID 19092984HCID 19092984, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-methoxymethoxymethyl-1-nitro-3,4,5-trimethoxy-benzene (6.03 g, 21 mmol) in ethanol (150 ml) was catalytically hydrogenated over 5% palladium on carbon (3 g) at 50 psi for 2 hours. The catalyst was removed by filtration through a pad of Celite, and the filtered catalyst was washed with ethanol. The combined filtrate and the washings are concentrated in vacuo to dryness, and the product was purified by column chromatography (SiO2, 4×25 cm, CHCl3) to give 4.82 g of 2-methoxymethoxymethyl-3,4,5-trimethoxyaniline (89.7%) as a syrup. 1H-NMR (CDCL3): δ3.42 (3H, s, CH2OMe), 3.77, 3.80, and 3.87 (each 3H, s, 3×OMe), 4.63 and 4.66 (each 2H, s, 2×CH2), 6.05 (1H, s, H-6). Analyses: Calculated for C12H19NO5 : C, 56.02; H, 7.44; N, 5.44. Found: C, 56.47; H, 7.05; N, 5.48.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. washthe filtered catalyst was washed with ethanol
  3. concentrationThe combined filtrate and the washings are concentrated in vacuo to dryness
  4. customthe product was purified by column chromatography (SiO2, 4×25 cm, CHCl3)

Sources & evidence

ORD record
ord-5afda26b9dbd490ca8cddaf858bdba3d
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

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