Hydroxyamine hydrochloride → HCID 53395917, compound

Hydroxylamine hydrochloride (0.574 g) was added portionwise to a solution of 1H-indole-6-carbaldehyde (1 g) in pyridine (5 ml) are RT. The resulting solution was heated to reflux and stirred at that temperature for 1 hour. The solvent was evaporated. The residue was diluted with ethyl acetate (50 mL) and the resulting solution was washed with aqueous hydrochloric acid (0.5 M, 40 mL). The organic fraction was separated and dried over anhydrous magnesium sulfate. The dried solution was concentrated to afford a brown oily solid. The residue was triturated with ether/hexane to afford 1H-indole-6-carbaldehyde oxime (D11) as a pink solid (128 mg). Solid was precipated out from the filtrate. The solid was collected to give another batch of 1H-indole-6-carbaldehyde oxime (D11) (818 mg). δH (DMSO-d6, 400 MHz): 6.44 (1H, m), 7.24 (1H, dd), 7.32 (1H, m), 7.55 (1H, dd), 7.57 (1H, s), 8.19 (1H, s), 10.88 (1H, s), 11.25 (1H, br s).

1. customare RT
2. temperatureThe resulting solution was heated
3. temperatureto reflux
4. customThe solvent was evaporated
5. additionThe residue was diluted with ethyl acetate (50 mL)
6. washthe resulting solution was washed with aqueous hydrochloric acid (0.5 M, 40 mL)
7. customThe organic fraction was separated
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationThe dried solution was concentrated
10. customto afford a brown oily solid
11. customThe residue was triturated with ether/hexane

ORD record

ord-59ca15c03cf444eb850aee4cec1a8992

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217028B2