Trifluoroacetic acid → HCID 20310365, compound

HRID 1763623Notes

Reaction equation

HRID 1763623 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])([O-])=O.FC(F)(F)C(O)=O.[H][H]>[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 20310370HCID 20310370, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20310365HCID 20310365, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture 10 g. of 6-[4-nitro-3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone in 50 ml. of trifluoroacetic acid is reduced with hydrogen and palladium on carbon to give 6-[4-amino-3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone. The preceding compound is converted to 6-[4-fluoro-3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone by the procedure described in J. Org. Chem., 26, 468 (1961). The preceding compound is reacted with phosphorus oxychloride as described in Example 47 to give 3-chloro-6-[4-fluoro-3-(trifluoromethyl)phenyl]pyridazine., which is reacted with formylhydrazine as described in Example 48 to give the product of the example.

Sources & evidence

ORD record
ord-5a5420ccdab845d0998e00e9d056e977
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

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