Hydrochloric Acid → HCID 178513238, compound

Temperature

50 °C

5-Cyanoindole (1.00 g), hydroxylamine.HCl (978 mg) and NaHCO3 (2.95 g) were dissolved/suspended in MeOH (14 ml), heated to 50° C. and stirred overnight. LCMS analysis showed the reaction was incomplete after this time so a further portion of hydroxylamine.HCl (978 mg) was added and the reaction temperature raised to 80° C. The reaction was complete after 4 hours. The reaction mixture was cooled to RT and evaporated to dryness under reduced pressure. The residue was treated with 1M aqueous HCl (50 ml) and extracted with EtOAc (2×50 ml). This failed to extract the product from the aqueous solution so it was treated with 2M aqueous NaOH to adjust the pH to approximately 7 then re-extracted with EtOAc (3×50 ml). The combined organics were washed with brine (30 ml), dried over MgSO4, filtered and evaporated to dryness to give the title compound (1.36 g) as a brown oil. δH (MeOD, 400 MHz) 6.50 (1H, s), 7.27 (1H, s), 7.36-7.45 (2H, m), 7.88 (1H, s). MS (ES): C9H8N3O requires 175; found 176 (MH+).

1. temperaturethe reaction temperature raised to 80° C
2. waitThe reaction was complete after 4 hours
3. temperatureThe reaction mixture was cooled to RT
4. customevaporated to dryness under reduced pressure
5. additionThe residue was treated with 1M aqueous HCl (50 ml)
6. extractionextracted with EtOAc (2×50 ml)
7. extractionto extract the product from the aqueous solution so it
8. additionwas treated with 2M aqueous NaOH
9. extractionthen re-extracted with EtOAc (3×50 ml)
10. washThe combined organics were washed with brine (30 ml)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. customevaporated to dryness

ORD record

ord-eb634173ea0843eb984c056b6da6814f

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101775B2