Methylamine → (6-Benzyloxy-3-nitroquinolinyl)methylamine

HRID 540844Notes

Reaction equation

[CH3:1][NH2:2].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]2Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([CH2:1][NH2:2])[C:15]([N+:21]([O-:23])=[O:22])=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methylamine (available as a 40% solution in water, 24 mL, 0.28 mol) was added to a solution of 6-benzyloxy-4-chloro-3-nitroquinoline (15.0 g, 48.5 mmol), prepared as described in Parts A-D of Example 2, in distilled water (300 mL), and the reaction was stirred at 100° C. for 1.5 hours. The reaction was allowed to cool to ambient temperature and stirred for four hours. A precipitate formed, which was isolated by filtration and washed with distilled water (3×60 mL). The solid was combined with material from another run and recrystallized from 2-propanol. The crystals were isolated by filtration, washed twice with cold hexanes, and dried for three days under high vacuum to provide 24.10 g of (6-benzyloxy-3-nitroquinolinyl)methylamine as yellow crystals.

Workup

customprepared
temperatureto cool to ambient temperature
stirringstirred for four hours
customA precipitate formed
customwhich was isolated by filtration
washwashed with distilled water (3×60 mL)
customrecrystallized from 2-propanol
customThe crystals were isolated by filtration
washwashed twice with cold hexanes
customdried for three days under high vacuum

Sources & evidence

ORD record: ord-e6a1149379fd4c158831583135fe8748
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871782B2

Reaction notes

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