Ethanol → HCID 178524018, compound

HRID 1090261Notes

Reaction equation

HRID 1090261 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1.[NH:14]1[C:22]2[C:17]3[C:18](=[CH:23][CH:24]=[CH:25][C:16]=3[C:15]1=S)[CH:19]=[CH:20][CH:21]=2.[OH-:27].[Na+].[CH2:29]([OH:31])C>>[CH:29]([OH:31])=[O:27].[N:5]1([CH2:4][CH2:3][CH2:2][NH:1][C:15]2[C:16]3[CH:25]=[CH:24][CH:23]=[C:18]4[C:17]=3[C:22](=[CH:21][CH:20]=[CH:19]4)[N:14]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

5

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 2304943HCID 2304943, compoundHCID 119591093-(1H-indazol-1-yl)propan-1-amine

Product 1

HCID 178524018HCID 178524018, compound

Procedure

A solution of 5.4 grams of N-(3-aminopropyl)indazole in 400 ml of ethanol was treated with 6.0 grams of benz(cd)indole-2-thione and then 11.0 grams of mercuric acetate. The mixture was then stirred under reflux for 8 hours. The black slurry was cooled to room temperature and treated with 7.5 ml of 10N sodium hydroxide. The reaction was filtered through a bed of celite, and the filtrate then concentrated to dryness in vacuo. The residue was partitioned between 250 ml of dichloromethane and 150 ml of water. The dichloromethane layer was concentrated to dryness. The residue was dissolved in 200 ml of acetone and the solution added to a stirred boiling solution of 6.0 grams of fumaric acid in 1200 ml of acetone. A precipitate formed at once. The reaction mixture was stirred at room temperature for two hours, the precipitate collected and dried. It melted at 163°-165° C. with decomposition.

Workup

  1. temperatureunder reflux for 8 hours
  2. filtrationThe reaction was filtered through a bed of celite
  3. concentrationthe filtrate then concentrated to dryness in vacuo
  4. customThe residue was partitioned between 250 ml of dichloromethane and 150 ml of water
  5. concentrationThe dichloromethane layer was concentrated to dryness
  6. dissolutionThe residue was dissolved in 200 ml of acetone
  7. additionthe solution added to a stirred
  8. customA precipitate formed at once
  9. stirringThe reaction mixture was stirred at room temperature for two hours
  10. customthe precipitate collected
  11. customdried

Sources & evidence

ORD record
ord-51ada0828e01452bbfdc9b1c9740677c
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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