2-Ethoxy-1-methoxy-4-nitro-benzene → 3,4-Diethoxyaniline

HRID 1297104Notes

Reaction equation

HRID 1297104 reaction equation
C(OC1C=C([N+]([O-])=O)C=CC=1OC)C.[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=1[O:27][CH2:28][CH3:29])[CH3:16]>>[CH2:28]([O:27][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:18]=1[O:17][CH2:15][CH3:16])[NH2:24])[CH3:29]

Participants

3

Reactant 2

HCID 117901432-Ethoxy-1-methoxy-4-nitro-benzeneHCID 133438301,2-Diethoxy-4-nitrobenzene

Product 1

HCID 5209363,4-DiethoxyanilineYield 80%

Procedure

By replacing 2-ethoxy-1-methoxy-4-nitrobenzene (XIXaa) in example XXaa by 1,2-diethoxy-4-nitrobenzene (XIXab) and proceeding in the same manner, the abovenamed product is obtained. Yield: 80%. 1H-NMR (CDCl3, 300 MHz): d 1.36–1.46 (m, 6H, 2 times —CH3), 3.44 (s, 2H exchangeable, —NH2), 3.97–4.07 (m, 4H, 2×OCH2), 6.19 (dd, 1H Ar), 6.23 (d, 1H Ar), 6.73 (d, 1H Ar).

Workup

  1. customthe abovenamed product is obtained

Sources & evidence

ORD record
ord-af93f9797b954389ad9c5280b0a39bf0
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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