Hydroxyamine hydrochloride → 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime

HRID 2409011Notes

Reaction equation

[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=O)[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl.[NH2:24][OH:25].CC([O-])=O.[Na+]>CO>[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=[N:24][OH:25])[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone (1.32 g, 4.2 mmol) in MeOH (50 mL) at RT was added hydroxylamine hydrochloride (877 mg, 12.61 mmol) followed by NaOAc (3.45 g, 42.0 mmol). The reaction mixture was stirred at 80° C. for 1 h then concentrated tinder reduced pressure. Water (100 mL) was added to the reaction mixture, and the mixture extracted with EtOAc (50 mL×3). The combined organic layers were concentrated under reduced pressure to afford 1.35 g (97.6%) of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime as yellow solid: MS (ESI) m/z: 320.1 [M+1]+.

Workup

concentrationthen concentrated tinder reduced pressure
additionWater (100 mL) was added to the reaction mixture
extractionthe mixture extracted with EtOAc (50 mL×3)
concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record: ord-823c9862ff26494195853edf6d603314
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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