(Phenylmethyl)hydrazine → HCID 10132921, compound

HRID 1935615Notes

Reaction equation

HRID 1935615 reaction equation
[C:1]([C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([NH:27][NH2:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(O)=O>[CH2:20]([N:27]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:1]([C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 11157(Phenylmethyl)hydrazineHCID 570996Ethyl 4-benzoylbenzoate

Product 1

HCID 10132921HCID 10132921, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 4-benzoylbenzoate (13.7 g, 54 mmole), benzylhydrazine (8 g, 65 mmole), ethanole (50 mL) and HOAc (1 mL) was refluxed for 12 hours and then treated with the procedure described in Example 1 to yield a crude product that was purified by column chromatography (silica gel-benzene), and recrystallized from n-hexane to give 4.8g 1-benzyl-3-(4′-ethoxycarbonylphenyl)indazole in a yield of 25.5%.

Workup

  1. temperaturewas refluxed for 12 hours
  2. additiontreated with the procedure
  3. customto yield a crude product that
  4. customwas purified by column chromatography (silica gel-benzene)
  5. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-1140354fdb734ac5b8b08edf8124f25a
Source dataset
uspto-grants-2002_05
Patent number
US06387942B2

Reaction notes

Loading…