Hydrazine hydrate (1:1) → 2'-Fluoro-4-hydroxy-5'-methoxy-[1,1'-biphenyl]-2-carbohydrazide

HRID 1049505Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:17]([O:19]CC)=O)=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1.O.[NH2:23][NH2:24]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:17]([NH:23][NH2:24])=[O:19])=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of ethyl 2′-fluoro-4-hydroxy-5′-methoxy-[1,1′-biphenyl]-2-carboxylate (1.37 g) in ethanol (15 mL) was added hydrazine monohydrate (4.47 mL), and the mixture was stirred at 95° C. for 46 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane and then methanol/ethyl acetate) to give the title compound (1.05 g) as a white amorphous solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane

Sources & evidence

ORD record: ord-e354724979a247fc848b55ed62c9a3d1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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