Benzonorbornene Synthesis via Radical Addition
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Solution Overview
Problem
The existing process for producing 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine involves numerous reaction steps, low yield, and an expensive ozonolysis reaction with triphenylphosphine, making it unsuitable for large-scale production.
Innovation Solution
A novel process involving the reaction of cyclopentadiene with CXCl3 in the presence of a radical initiator or metal catalyst, followed by base treatment and hydrogenation, reduces the number of steps and eliminates costly reagents, resulting in higher yields and improved economic viability.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If the known multi-step process is used to prepare 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine, then the product can be obtained, but the yield decreases and the production cost increases due to numerous reaction steps and expensive reagents
Solution Approach 1:
The patent combines multiple reaction steps into a single step by reacting cyclopentadiene with CXCl3 in the presence of a radical initiator or metal catalyst to directly form the target compound, eliminating the need for separate hydrogenation, ozonolysis, and other intermediate steps in the known process
Solution Approach 2:
The patent extracts and eliminates the expensive and complex ozonolysis step along with triphenylphosphine from the synthesis route, replacing it with a simpler radical initiation or metal-catalyzed approach that achieves the same transformation more efficiently
2Ease of manufacture
If the known process using ozonolysis and triphenylphosphine is used, then the product can be prepared, but the production cost increases significantly and the process becomes unsuitable for large-scale production
Solution Approach 1:
The patent replaces expensive reagents such as triphenylphosphine and ozone with cheaper alternatives like radical initiators (e.g., peroxides, azo compounds) or metal catalysts that can be used in smaller amounts and are more suitable for industrial scaling
Solution Approach 2:
The patent changes the reaction conditions and reagents from the original known process, using different chemical parameters (radical initiators, metal catalysts, solvent systems) to achieve the same product through a more economical and scalable pathway
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The new process achieves high yields and good quality production of 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine with fewer reaction steps and without the need for expensive triphenylphosphine, making it economically advantageous for large-scale production.
Implementation Method 1
reacting cyclopentadiene with CXCl3, wherein X is chloro or bromo, in the presence of a radical initiator to a compound of formula II
Implementation Method 2
reacting cyclopentadiene with CXCl3, wherein X is chloro, in the presence of a metal catalyst to a compound of formula II
Implementation Method 3
reacting the compound of formula II with a base in an appropriate solvent to the compound of formula III
Implementation Method 4
converting the compound of formula III in the presence of 1,2-dehydro-6-nitrobenzene to the compound of formula IV
Implementation Method 5
hydrogenating the compound of formula IV with a hydrogen source in the presence of a metal catalyst
Data Source
AI summary
The present invention relates to a novel a process for the preparation of 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine which process comprises a) reacting cyclopentadiene in the presence of a radical initiator and CXCl3, wherein X is chloro or bromo, to a compound of formula I1, or aa) reacting cyclopentadiene with CXCl3, wherein X is chloro, in the presence of a metal catalyst to a compound of formula I1, wherein X is chloro, b) reacting the compound of formula I1 with a base in the presence of an appropriate solvent to the compound of formula III, c) and converting the compound of formula III in the presence of 1,2-dehydro-6-nitrobenzene to the compound of formula IV, and d) hydrogenating the compound of formula IV in the presence of a metal catalyst.