Hydroxylamine → 3-[4-(hydroxycarbamoyl)butyl]-N-(3-pyridyl)indole

HRID 485357Notes

Reaction equation

HRID 485357 reaction equation
[NH2:1][OH:2].C[O:4][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)=O>CO>[OH:2][NH:1][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)=[O:4]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 20270179HCID 20270179, compound

Product 1

HCID 202702083-[4-(hydroxycarbamoyl)butyl]-N-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of hydroxylamine (from 2.06 g of hydroxylamine hydrochloride and 2.02 g of sodium hydroxide) and 7.6 g of 3-(4-methoxycarbonylbutyl)-N-(3-pyridyl)indole in 25 ml of methanol is allowed to stand at room temperature for 20 hours. The methanol is evaporated and the residue is taken up in 5 ml of water and adjusted to pH=7. The mixture is extracted with methylene chloride, the extract is washed with water, dried and evaporated to dryness yielding 3-[4-(hydroxycarbamoyl)butyl]-N-(3-pyridyl)indole.

Workup

  1. customThe methanol is evaporated
  2. extractionThe mixture is extracted with methylene chloride
  3. washthe extract is washed with water
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8c9a4f12ed6b43fe8cb59a21b8a8bd6c
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

Loading…