Hydroxyamine hydrochloride → 2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-9-hydroxyimino-10-methyl-(9H,10H)-acridine

HRID 61976Notes

Reaction equation

[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][N:4]([S:9]([C:12]2[CH:25]=[CH:24][C:23]3[N:22]([CH3:26])[C:21]4[C:16](=[CH:17][C:18]([S:27]([N:30]5[CH2:35][CH:34]([CH3:36])[CH2:33][CH:32]([CH3:37])[CH2:31]5)(=[O:29])=[O:28])=[CH:19][CH:20]=4)[C:15](=S)[C:14]=3[CH:13]=2)(=[O:11])=[O:10])[CH2:3]1.Cl.[NH2:40][OH:41]>N1C=CC=CC=1>[CH3:37][CH:32]1[CH2:33][CH:34]([CH3:36])[CH2:35][N:30]([S:27]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([CH3:26])[C:23]4[C:14](=[CH:13][C:12]([S:9]([N:4]5[CH2:5][CH:6]([CH3:8])[CH2:7][CH:2]([CH3:1])[CH2:3]5)(=[O:11])=[O:10])=[CH:25][CH:24]=4)[C:15](=[N:40][OH:41])[C:16]=3[CH:17]=2)(=[O:28])=[O:29])[CH2:31]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2,7-bis(3,5-dimethylpiperidin-1-ylsulfonyl)-10-methylacridine-9(10H)-thione (290 mg, 0.5 mmole) in pyridine (5 mL) was added hydroxylamine hydrochloride (210 mg, 30 mmole) and the mixture was stirred at 100° C. for 8 hrs. Solvent was removed and the residue was treated with water to remove excess of hydroxylamine. Crude material was crystallized from methanol-water to give 245 mg (85%) of the title compound. MS 575 (MH+).

Workup

customSolvent was removed
additionthe residue was treated with water
customto remove excess of hydroxylamine
customCrude material was crystallized from methanol-water

Sources & evidence

ORD record: ord-deb1d4259fd04b7fbad1cb85b2ecfffd
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09446021B2

Reaction notes

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