Hydrochloric Acid → 4-[3-Hydroxy-2-(4-nitro-pyrazol-1-yl)-propyl]-6-methoxy-quinolin-3-ol

HRID 1422906Notes

Reaction equation

[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]1[O:12][C:11](=[O:19])[C:10]([N:20]3[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[N:21]3)=[CH:9][C:8]2=1.Cl.CO>O1CCCC1>[OH:19][CH2:11][CH:10]([N:20]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[N:21]1)[CH2:9][C:8]1[C:7]2[C:16](=[CH:17][CH:18]=[C:5]([O:4][CH3:3])[CH:6]=2)[N:15]=[CH:14][C:13]=1[OH:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium borohydride (179 mg, 4.73 mmol, 8.0 eq) is added at 0° C. to a stirred solution of 6-methoxy-3-(4-nitro-pyrazol-1-yl)-1-oxa-9-aza-phenanthren-2-one (200 mg, 0.59 mmol, 1.0 eq) in tetrahydrofuran (50 mL). After 2 hours stirring at 0° C., the reaction mixture is cautiously acidified to pH=1 with a 4N hydrochloric acid aqueous solution. Tetrahydrofuran is evaporated and the residue is extracted with ethyl acetate (3×40 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: petroleum ethyl acetate:methanol, 20:1, v/v) to afford 4-[3-hydroxy-2-(4-nitro-pyrazol-1-yl)-propyl]-6-methoxy-quinolin-3-ol as a white solid (170 mg, 84% yield).

Workup

customTetrahydrofuran is evaporated
extractionthe residue is extracted with ethyl acetate (3×40 mL)
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a residue that
customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record: ord-c7abfe82ae1444d393fc99f09febfdc5
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927541B2

Reaction notes

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