Pyridine → 1-tosyl-1H-indole-4-carbaldehyde oxime

HRID 475183Notes

Reaction equation

[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=O)[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.[NH2:23][OH:24].N1C=CC=CC=1>CCO>[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[N:23][OH:24])[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: 70 °C

Procedure

To a solution of 42 (900 mg, 3 mmol) in EtOH (10 mL) was added hydroxylamine hydrochloride (1.0 g, 15 mmol) and pyridine (1.0 mL). After the reaction mixture was stirred at 70° C. overnight, the solvent was removed in vacuo to afford 800 mg (85%) of 1-tosyl-1H-indole-4-carbaldehyde oxime (44) as white solid: MS (ESI) m/z=315 [M+1]+.

Workup

customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-40ea97fd2cd847f084ce7715e43f56d0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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