Ethylenediamine → 4-Amino-3-fluorobenzonitrile
Reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[Cu][C:11]#[N:12].C(N)CN>CN1C(=O)CCC1>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:11]#[N:12])=[CH:3][C:4]=1[F:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In NMP, compound [O], commercially available 4-bromo-2-fluoroaniline is cyanated with copper (I) cyanide and the resulting copper complex is decomposed with ethylene diamine (EDA) to yield compound [P], 4-amino-3-fluorobenzonitrile. Compound [P] is reacted with nitrosyl hydrogen sulfate (HSO4 --ONO2), prepared by mixing sodium nitrite and concentrated sulfuric acid in glacial acetic acid, and converted into the corresponding diazonium salt. The diazonium salt is brominated with copper (I) bromide in hydrobromic acid to yield compound [Q], 4-bromo-3-fluorobenzonitrile. Compound [Q] is reacted with gaseous hydrogen chloride in anhydrous ethanol to yield compound [R], 4-bromo-3-fluorobenzimidate hydrogen chloride. In ethanol, compound [R] is reacted with gaseous ammonia to yield compound [S], 4-bromo-3-fluorobenzamidine hydrogen chloride.
Sources & evidence
- ORD record
- ord-465d3522d6114381a3a4c824dacda55d
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05200110
Reaction notes
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