Hydroxyamine hydrochloride → N'-Hydroxy-(5-bromo-1H-3-indolyl)ethanimidamide

HRID 330280Notes

Reaction equation

HRID 330280 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][C:18]#[N:19]>CO.O>[OH:6][N:5]=[C:18]([NH2:19])[CH2:17][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([Br:7])[CH:9]=2)[NH:13][CH:12]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 138059442-(5-bromo-1H-indol-3-yl)acetonitrile

Product 1

HCID 54095585N'-Hydroxy-(5-bromo-1H-3-indolyl)ethanimidamideYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of sodium methoxide (16.92 mL, 0.074 mol, 25 wt %/methanol) in methanol (120 mL) was added powdered hydroxylamine hydrochloride (5.66 g, 0.0814 mol). The mixture was heated at reflux for 1 hour. 5-Bromo-3-indolylacetonitrile (8.8 g, 0.37 mol) was added and refluxing was continued overnight. Refluxing was continued for a further 3 hours. The reaction was cooled to room temperature and concentrated under reduced pressure to obtain a pale yellow solid. The solid was suspended in water (100 mL), stirred for 1/2 hour, filtered, air dried and stirred in ether (40 mL) to give 7.91 g (71%) of product as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturerefluxing
  4. temperatureRefluxing
  5. waitwas continued for a further 3 hours
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a pale yellow solid
  8. filtrationfiltered
  9. customair dried
  10. stirringstirred in ether (40 mL)

Sources & evidence

ORD record
ord-bb75fefe4de9458c9b7d2a45ee84514c
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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