Hydrazine → 3-Hydroxy-4-methylbenzohydrazide

Reaction equation

C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([OH:12])[CH:6]=1)C.[NH2:14][NH2:15]>>[OH:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[CH3:11])[C:4]([NH:14][NH2:15])=[O:3]

Participants

Reactant 2

HCID 9321Hydrazine

HCID 15745489Ethyl 3-hydroxy-4-methylbenzoate

Product 1

HCID 167809363-Hydroxy-4-methylbenzohydrazide

Conditions

Temperature: 150 °C

Procedure

A suspension of ethyl 3-hydroxy-4-methylbenzoate (14.42 g, 80 mmol) (from Example 2 supra) in anhydrous hydrazine (30 mL, 956 mmol) (Aldrich) was heated at reflux (150° C. bath temperature) for 2.0 hours. After cooling to room temperature, mixture was concentrated under reduced pressure (high vacuum) to give crude 3-hydroxy-4-methyl-benzoic acid hydrazide as an off-white solid. (Yield 13.26 g, 100%).

Workup

temperaturewas heated
temperatureAfter cooling to room temperature
concentrationmixture was concentrated under reduced pressure (high vacuum)

Sources & evidence

ORD record: ord-b248f8cb9e5145f3b20e5416e2e22c05
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

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