Ethanol → 1-(3-Hydroxy-5-aminobenzoyl)-2-benzoylhydrazine

HRID 431388Notes

Reaction equation

HRID 431388 reaction equation
C1C2C(=CC=CC=2)C=CC=1C[O:12][C:13]1[CH:14]=[C:15]([CH:28]=[C:29]([N+:31]([O-])=O)[CH:30]=1)[C:16]([NH:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17].CCO>[Pd].CN(C=O)C>[OH:12][C:13]1[CH:14]=[C:15]([CH:28]=[C:29]([NH2:31])[CH:30]=1)[C:16]([NH:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17]

Participants

5

Reactant 2

HCID 702EthanolHCID 187634381-{3-[(2-Naphthyl)methoxy]-5-nitrobenzoyl)-2-benzoylhydrazine

Product 1

HCID 187634351-(3-Hydroxy-5-aminobenzoyl)-2-benzoylhydrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-{3-[(2-naphthyl)methoxy]-5-nitrobenzoyl}-2-benzoylhydrazine (0.34 g, 0.77 mmol), Pd/C (10%, 0.35 g), EtOH (10 mL), and DMF (10 mL) was hydrogenated in Parr apparatus (H2 pressure—30 psi) at room temperature for 1.5 h. Catalyst was filtered off, and filtrate concentrated in vacuo to give a slurry of white needles, which were filtered and washed with EtOH (3×25 mL). Yield 0.20 g (96%). 1H NMR (DMSO-d6, 400 MHz), δ: 10.37 (s, 1H); 10.12 (s, 1H); 9.20 (s, 1H); 7.91 (d, J=7.0 Hz, 2H); 7.62-7.48 (m, 3H); 6.54 (s, 1H); 5.46 (s, 1H); 6.19 (s, 1H); 5.18 (br.s, 2H).

Workup

  1. filtrationCatalyst was filtered off
  2. concentrationfiltrate concentrated in vacuo
  3. customto give a slurry of white needles, which
  4. filtrationwere filtered
  5. washwashed with EtOH (3×25 mL)

Sources & evidence

ORD record
ord-3997371e0938483bb07d70e5bbfe207b
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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