Hydrazine hydrate (1:1) → HCID 66618790, compound

HRID 406338Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][O:12][C:11](=[O:15])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.O.[NH2:19][NH2:20]>C(O)C>[OH:12][CH2:13][CH2:14][CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:4]=1)[CH2:10][C:11]([NH:19][NH2:20])=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

4-(3-Trifluoromethylphenyl)tetrahydropyran-2-one (2.5 g) was dissolved in ethanol (10 mL), and hydrazine monohydrate (4.96 mL) was added at room temperature. The mixture was stirred at 80° C. for 4.5 hours and then concentrated under reduced pressure. The resulting oil was partitioned with methylene chloride and water. The aqueous layer was extracted with methylene chloride five times. After drying over magnesium sulfate, concentration under reduced pressure and purification by silica gel column chromatography (amino silica gel, mobile phase:ethyl acetate/heptane=0 to 50%→methanol/ethyl acetate=10%) gave the title compound (1.55 g).

Workup

concentrationconcentrated under reduced pressure
customThe resulting oil was partitioned with methylene chloride and water
extractionThe aqueous layer was extracted with methylene chloride five times
dry with materialAfter drying over magnesium sulfate, concentration under reduced pressure and purification by silica gel column chromatography (amino silica gel, mobile phase:ethyl acetate/heptane=0 to 50%→methanol/ethyl acetate=10%)

Sources & evidence

ORD record: ord-5cd1cc4a0ba948db9e5f2d7bcac76f5c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754100B2

Reaction notes

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