Isoamyl Nitrite → 5-Amino-2-chloro-4-fluorobenzoyl cyanide oxime sodium salt

HRID 1709778Notes

Reaction equation

HRID 1709778 reaction equation
[Na:1].[NH2:2][C:3]1[C:4]([F:13])=[CH:5][C:6]([Cl:12])=[C:7]([CH:11]=1)[CH2:8][C:9]#[N:10].C([O:19][N:20]=O)CC(C)C>C(O)C>[Na:1].[NH2:2][C:3]1[C:4]([F:13])=[CH:5][C:6]([Cl:12])=[C:7]([C:8](=[N:20][OH:19])[C:9]#[N:10])[CH:11]=1

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 5360545SodiumHCID 230367472-(5-Amino-2-chloro-4-fluorophenyl)acetonitrile

Product 1

HCID 867429495-Amino-2-chloro-4-fluorobenzoyl cyanide oxime sodium salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.3 g of sodium in 20 ml of absolute ethanol is introduced, with stirring, into a three-necked flask. There are then added slowly dropwise at room temperature, with stirring, firstly 1.8 g of 5-amino-2-chloro-4-fluorobenzyl cyanide and subsequently 1.5 ml of isopentylnitrite. The reaction solution is stirred at room temperature for a further 15 hours, and afterwards concentrated by evaporation. The residue is is taken up in glacial acetic acid, stirred up and filtered to thus obtain 2.2 g of the sodium salt of 5-amino-2-chloro-4-fluorobenzoyl cyanide which melts at 263°-264° C.

Workup

  1. additionThere are then added slowly dropwise at room temperature
  2. stirringwith stirring
  3. stirringThe reaction solution is stirred at room temperature for a further 15 hours
  4. concentrationafterwards concentrated by evaporation
  5. stirringstirred up
  6. filtrationfiltered to thus obtain 2.2 g of the sodium salt of 5-amino-2-chloro-4-fluorobenzoyl cyanide which melts at 263°-264° C.

Sources & evidence

ORD record
ord-4e67201b4716452ab14457a2de830eb2
Source dataset
uspto-grants-1990_08
Patent number
US04950777

Reaction notes

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