Hydroxyamine hydrochloride → N'-Hydroxy-2-oxoindoline-5-carboxamidine

HRID 598883Notes

Reaction equation

HRID 598883 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)#[N:2].Cl.[NH2:14][OH:15].C(=O)(O)[O-].[Na+]>CO>[OH:15][N:14]=[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)[NH2:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrile

Product 1

HCID 76673478N'-Hydroxy-2-oxoindoline-5-carboxamidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 5-cyanooxindole (5.00 g, 32 mmol) (commercially available from the Combi-Blocks Catalog (Order Number IN-0073), hydroxylamine hydrochloride (4.4 g, 63 mmol), and sodium bicarbonate (11 g, 126 mmol) in 50 mL anhydrous MeOH was heated to 65° C. After 12 hours, the reaction was complete. The mixture was cooled and the suspension was filtered. The resulting solid was washed with 50 mL MeOH. The solid was transferred into a 500 mL round bottom flask and 200 mL distilled water was added. The resulting suspension was sonicated for 5 minutes. Filtration gave the desired compound as an off white solid (5.3 g, 88%). MS (API-ES) m/z (%): 192.0 (100%, M++H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe suspension was filtered
  3. washThe resulting solid was washed with 50 mL MeOH
  4. customThe solid was transferred into a 500 mL round bottom flask
  5. distillation200 mL distilled water
  6. additionwas added
  7. customThe resulting suspension was sonicated for 5 minutes
  8. filtrationFiltration

Sources & evidence

ORD record
ord-73fdd3bf6e9448199c5c55325786531a
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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