Phosphorus oxychloride → HCID 20310382, compound

HRID 1763624Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=O)[NH:12][N:13]=2)=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:11]1[N:12]=[N:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:15]([F:18])([F:17])[F:16])[CH:4]=2)=[CH:9][CH:10]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 20310376HCID 20310376, compound

Product 1

HCID 20310382HCID 20310382, compound

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-37b55055fe2249b592152c2f2143f120
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04112095

Reaction notes

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