Acetic Acid → 7-(2-Nitrophenyl)benz[g]indole

HRID 617809

Reaction equation

HRID 617809 reaction equation
Cl.[C:2]1([NH:12]N)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1CC=O)([O-:16])=[O:15].Cl.[C:27](O)(=O)[CH3:28]>>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:8]1[CH:9]=[CH:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]1[C:2]=2[NH:12][CH:28]=[CH:27]1)([O-:16])=[O:15]

Participants

5

Reactant 4

HCID 176Acetic Acid3×HCID 313Hydrochloric AcidHCID 519949Hydrazine, 1-naphthalenyl-, hydrochloride (1:1)HCID 108447642-Nitrobenzeneacetaldehyde

Product 1

HCID 218499067-(2-Nitrophenyl)benz[g]indoleYield 32%

Procedure

A suspension of 4.24 g (22.5 mmol) of 1-naphthylhydrazine hydrochloride in acetic acid (35 ml) was slowly boiled and a solution of 3.4 g (20.6 mmol) of 2-nitrophenylacetaldehyde in acetic acid (15 ml) was dropped thereinto under stirring. After the completion of the dropping, the obtained mixture was heated under reflux for 1 hour. Then 20 ml of a mixture of 1 N hydrochloric acid with acetic acid was further added thereto and the obtained mixture was heated under reflux for additional 1 hour. After distilling off the solvent, the residue was dissolved by adding ethyl acetate thereto. The organic layer was washed successively with an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography to thereby give 1.91 g (yield: 32%) of 7-(2-nitrophenyl)benz[g]indole. Then the obtained product was dissolved in ethyl acetate (60 ml) and 200 mg of platinum (IV) oxide was added thereto. Then catalytic reduction was effected under atmospheric pressure in a hydrogen atmosphere at room temperature to thereby give 1.7 g (yield: 99%) of 7-(2-aminophenyl)benz[g]indole.

Workup

  1. temperatureAfter the completion of the dropping, the obtained mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturethe obtained mixture was heated
  4. temperatureunder reflux for additional 1 hour
  5. distillationAfter distilling off the solvent
  6. dissolutionthe residue was dissolved
  7. additionby adding ethyl acetate
  8. washThe organic layer was washed successively with an aqueous solution of sodium hydrogencarbonate, water
  9. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  10. distillationAfter distilling off the solvent
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e85167dfcd2a45afba45b2d9766de9a2
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Linked notes

Loading…