Hydrazine → 3-Chloro-4-hydroxybenzohydrazide

HRID 563246Notes

Reaction equation

HRID 563246 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([Cl:12])[CH:6]=1)C.[NH2:14][NH2:15]>>[Cl:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[OH:11])[C:4]([NH:14][NH2:15])=[O:3]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 12652105Ethyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 109542683-Chloro-4-hydroxybenzohydrazideYield 69%

Procedure

Ethyl-3-chloro-4-hydroxybenzoate (4.95 g, 25 mmol) was reacted with hydrazine as described for the preparation of intermediate 22b to afford the product as white crystals (3.15 g, 69%). 1H NMR (400 MHz, DMSO-d6, δ in ppm) 10.71 (br s, 1H), 9.64 (br s, 1H), 7.83 (d, J=2.1 Hz, 1H), 7.65 (dd, J=2.1, 8.4 Hz, 1H), 6.99 (d, J=8.4 Hz, 1H), 4.43 (br s, 2H).

Sources & evidence

ORD record
ord-45c3383f12814359a09a474e5c22de61
Source dataset
uspto-grants-2011_11
Patent number
US08067448B2

Reaction notes

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