Benzeneacetic acid, hydrazide → HCID 16075311, compound

HRID 1795112Notes

Reaction equation

HRID 1795112 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=O)=[CH:4][CH:3]=1.[C:17]1([CH2:23][C:24]([NH:26][NH2:27])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCO>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2/[CH:9]=[N:27]/[NH:26][C:24](=[O:25])[CH2:23][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70301Benzeneacetic acid, hydrazideHCID 14748712-(4-methylphenoxy)benzaldehyde

Product 1

HCID 16075311HCID 16075311, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-methylphenoxy)-benzaldehyde (500 mg, 2.36 mmol) in EtOH (10 mL) is added phenyl acetic hydrazide (336 mg, 2.36 mmol) and the reaction is heated to 80° C. for 1 h. While cooling a white precipitate forms, and this solid is isolated by filtration and washed with portions of EtOH and Et2O. This solid is dried under vacuum to provide N′-{(1E)-[2-(4-methylphenoxy)phenyl]methylene)}2-phenylacetohydrazide (432 mg, 22%). 1H-NMR (400 MHz, DMSO-d6) 11.70–11.55 (m, 1H), 8.51–8.33 (m, 1H), 8.00–7.92 (m, 1H), 7.42–7.19 (m, 9H), 6.91–6.85 (m, 3H), 3.98–3.43 (m, 2H), 2.29 (s, 3H). ESI+ for C22H20N2O2: m/z=345 (M+H)+.

Workup

  1. temperatureWhile cooling a white precipitate forms
  2. customthis solid is isolated by filtration
  3. washwashed with portions of EtOH and Et2O
  4. customThis solid is dried under vacuum
  5. customto provide N′-{(1E)-[2-(4-methylphenoxy)phenyl]methylene)}2-phenylacetohydrazide (432 mg, 22%)

Sources & evidence

ORD record
ord-8685dc68bb1142f9944892d4587bfeae
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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