Hydrazine hydrate (1:1) → HCID 178514433, compound

Temperature

120 °C

A mixture of trans-4-(3-chloro-phenoxy)-cyclohexanecarboxylic acid methyl ester (0.25 g, 0.93 mmol) and hydrazine hydrate (0.044 ml, 0.91 mmol) was heated at 120° C. for 22 h. Addition of further hydrazine hydrate (0.020 ml, 0.42 mmol) was followed by stirring at 120° C. for 5 h. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate (50 ml) and 1 M aqueous sodium hydroxide solution (50 ml). The layers were separated and the aqueous layer was extracted with a 50-ml portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound (0.21 g, 86%) as white solid, which was used in the next step without further purification. MS m/e: 269 (M+H+)

1. temperatureAfter cooling to room temperature the reaction mixture
2. customwas partitioned between ethyl acetate (50 ml) and 1 M aqueous sodium hydroxide solution (50 ml)
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with a 50-ml portion of ethyl acetate
5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-53c47a1f56dd4badbebca787504c6bc2

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461152B2