Sodium Bicarbonate → N-methyl-N-(2-ethoxycarbonylbenzyl)-3-ethoxycarbonylmethylaniline

HRID 904186Notes

Reaction equation

HRID 904186 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:4]=1.C(=O)([O-])O.[Na+].Br[CH2:21][C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]>O>[CH3:1][N:2]([CH2:21][C:22]1[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11032082Ethyl 2-(bromomethyl)benzoateHCID 23333594Ethyl 2-[3-(methylamino)phenyl]acetate

Product 1

HCID 23333589N-methyl-N-(2-ethoxycarbonylbenzyl)-3-ethoxycarbonylmethylanilineYield 68.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material employed above had been synthesized in the same manner as described in Example 1. That is, N-methyl-3-ethoxycarbonylmethylaniline (20.7 g), sodium hydrogencarbonate (19 g), water (30 ml) and ethyl 2-bromomethylbenzoate (27.5 g) were used to produce N-methyl-N-(2-ethoxycarbonylbenzyl)-3-ethoxycarbonylmethylaniline (26 g) as a light yellow oil. Then, N-methyl-N-(2-ethoxycarbonylbenzyl)-3-ethoxycarbonylmethylaniline (26 g) so produced, sodium hydroxide (40 g), water (450 ml) and ethanol (150 ml) were used to prepare N-methyl-N-(2-carboxybenzyl)-3-carboxymethylaniline (14.8 g).

Workup

  1. customabove had been synthesized in the same manner

Sources & evidence

ORD record
ord-b81e8a66721f4dd297a595f6a93d028c
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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