Oxalic Acid → N-(3-chloro-2-propenyl)-N-methyl-1-naphthalene-methanamine oxalate

HRID 1182425Notes

Reaction equation

HRID 1182425 reaction equation
[Cl:1][CH:2]=[CH:3][CH2:4][N:5]([CH3:17])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[C:18]([OH:23])(=[O:22])[C:19]([OH:21])=[O:20]>CO>[C:18]([OH:23])(=[O:22])[C:19]([OH:21])=[O:20].[Cl:1][CH:2]=[CH:3][CH2:4][N:5]([CH3:17])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 53928283N-(3-chloro-2-propenyl)-N-methyl-1-naphthalenemethanamine

Product 1

HCID 86604117N-(3-chloro-2-propenyl)-N-methyl-1-naphthalene-methanamine oxalateYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 ml 4-necked round-bottom flask equipped with thermometer and magnetic stirrer, under nitrogen atmosphere, is loaded with 80 g of N-(3-chloro-2-propenyl)-N-methyl-1-naphthalenemethanamine (325 mmoles) (E/Z=80/20) and 317 g of methanol at room temperature. The resulting solution is added with 29.3 g of oxalic acid (325 mmoles), keeping stirring for 15′, then the precipitate is filtered and the product is washed with methanol on the filter. 94.0 g of N-(3-chloro -2-propenyl)-N-methyl-1-naphthalene-methanamine oxalate (279.9 mmoles) are obtained, 86% (E/Z=80/20) molar yield.

Workup

  1. customA 500 ml 4-necked round-bottom flask equipped with thermometer and magnetic stirrer, under nitrogen atmosphere
  2. filtrationis filtered
  3. washthe product is washed with methanol on the filter

Sources & evidence

ORD record
ord-c8e3c042d10343c791c3a340f6646927
Source dataset
uspto-grants-2007_10
Patent number
US07288678B2

Reaction notes

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