Acetic Acid → beta-Methoxy-beta-(3-nitro-2,4,6-trimethylphenylhydrazino)-acrylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]([O:11][CH3:12])(OC)OC)[CH3:2].C(O)(=O)C.[N+:18]([C:21]1[C:22]([CH3:31])=[C:23]([NH:29][NH2:30])[C:24]([CH3:28])=[CH:25][C:26]=1[CH3:27])([O-:20])=[O:19]>CO>[CH2:1]([O:3][C:4](=[O:13])[CH:5]=[C:6]([O:11][CH3:12])[NH:30][NH:29][C:23]1[C:24]([CH3:28])=[CH:25][C:26]([CH3:27])=[C:21]([N+:18]([O-:20])=[O:19])[C:22]=1[CH3:31])[CH3:2]Participants
Procedure
26.9 g (0.14 mol) of trimethoxypropionic acid ethyl ester (prepared according to DT-OS 2,042,920 ) are dissolved in 100 ml of absolute methanol, 7 ml of glacial acetic acid are added and the mixture is heated to the boil. 23.4 g (0.12 mol) of 3-nitro-2,4,6-trimethylphenylhydrazine (prepared according to DT-OS 2,156,913) are introduced in portions into the mixture over the course of 10 minutes. The mixture is stirred for a further 10 minutes at the boil and is allowed to cool whilst stirring. The orange crystals which have precipitated are filtered off, washed with a little methanol and dried (18 hours in vacuo at 50° C.). 14.4 g of β-methoxy-β-(3-nitro-2,4,6-trimethylphenylhydrazino)-acrylic acid ethyl ester of melting point 82° - 83° C. are obtained.
Workup
- temperaturethe mixture is heated to the boil
- temperatureto cool
- stirringwhilst stirring
- customThe orange crystals which have precipitated
- filtrationare filtered off
- washwashed with a little methanol
- customdried (18 hours in vacuo at 50° C.)
Sources & evidence
- ORD record
- ord-cdbbb438b1724c988fce83aac6e98ad7
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04026709
Reaction notes
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