Hydrazine hydrate (1:1) → HCID 86673686, compound

HRID 244384Notes

Reaction equation

HRID 244384 reaction equation
O.[NH2:2][NH2:3].[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16](O)([CH3:17])[O:15][C:14](=O)[C:13]=2[C:20]2[C:25]([F:26])=[CH:24][C:23]([F:27])=[CH:22][C:21]=2[F:28])=[CH:8][CH:7]=1)#[CH:5]>C(O)CCC>[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([CH3:17])=[N:3][NH:2][C:14](=[O:15])[C:13]=2[C:20]2[C:25]([F:26])=[CH:24][C:23]([F:27])=[CH:22][C:21]=2[F:28])=[CH:8][CH:7]=1)#[CH:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 60200154HCID 60200154, compound

Product 1

HCID 86673686HCID 86673686, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Hydrazine hydrate (0.17 g) is added to a solution of 0.87 g 4-(4-ethynylphenyl)-5-hydroxy-5-methyl-3-(2,4,6-trifluorophenyl)-5H-furan-2-one in 5 ml of 1-butanol and this mixture is heated for 4 h to 120° C. The reaction mixture is evaporated under reduced pressure and the residue is purified by chromatography on silica gel, using a mixture of toluene/ethyl acetate 5:1 as eluent to obtain 5-(4-ethynylphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-2H-pyridazin-3-one (Compound No. 1) as colourless crystals, m.p. 252-254° C.

Workup

  1. temperaturethis mixture is heated for 4 h to 120° C
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customthe residue is purified by chromatography on silica gel
  4. additiona mixture of toluene/ethyl acetate 5:1 as eluent

Sources & evidence

ORD record
ord-8c4801018492412792b98ec01970db62
Source dataset
uspto-grants-2014_02
Patent number
US08658644B2

Reaction notes

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