3-Nitrophenylacetonitrile → (3-Amino-phenyl)-acetonitrile
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][C:8]#[N:9])([O-])=O.[H][H]>S(=O)(=O)(O)O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][C:8]#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A correspondingly substituted benzyl cyanide of the formula Ve is nitrated in concentrated sulfuric acid. The formed 3-nitrobenzyl cyanide of the formula Vf is subsequently hydrogenated in the presence of a catalyst with hydrogen to obtain 3-aminobenzyl cyanide of the formula Vg. By treatment with isopentyl nitrite in the presence of sodium and ethanol, there is formed the Na salt of 3-aminobenzoyl cyanide oxime of the formula Vh, which is reacted with an ester of the formula VIII to obtain 3-aminophenoxime ether of the formula Va. This can be subjected to a condensation reaction, as described above, with the 3,4,5,6-tetrahydrophthalic anhydride of the formula II.
Sources & evidence
- ORD record
- ord-02621c5e76a04003bffbc14b35953a91
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04824476
Reaction notes
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