Hydrazine hydrate (1:1) → 3-Amino-4-methylbenzohydrazide

Temperature

100 °C

Into a round-bottom flask, was placed a solution of methyl 3-amino-4-methylbenzoate (6.60 g, 40.0 mmol, 1.00 equiv) in ethanol (100 mL). Hydrazine hydrate (10.0 g, 200 mmol, 5.00 equiv) was added to the reaction. The resulting solution was stirred for 2 h at 100° C. in an oil bath. After cooling to ambient temperature, the mixture was concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate (20 mL). The aqueous layer was extracted with 4×20 mL of ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate, concentrated under reduced pressure, and dried under high-vacuum to yield 4.60 g (70%) of the title compound as a brown solid.

1. customInto a round-bottom flask, was placed
2. temperatureAfter cooling to ambient temperature
3. concentrationthe mixture was concentrated under reduced pressure
4. customThe residue was partitioned between water and ethyl acetate (20 mL)
5. extractionThe aqueous layer was extracted with 4×20 mL of ethyl acetate
6. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customdried under high-vacuum

ORD record

ord-44d2720299394f7f8f158beafd25f892

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2