Sodium Chloride → HCID 86617186, compound

HRID 1993464Notes

Reaction equation

[OH:1][C@@H:2]1[C:15]([CH3:17])([CH3:16])[O:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([C:18]#[N:19])[CH:7]=[CH:6]3)[C@H:3]1[NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-:29].[K+].[Cl-].[Na+]>C(O)(C)(C)C>[OH:1][C@@H:2]1[C:15]([CH3:17])([CH3:16])[O:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([C:18]([NH2:19])=[O:29])[CH:7]=[CH:6]3)[C@H:3]1[NH:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (±)-trans-2-hydroxy-3,3-dimethyl-1-[(2-phenylethyl)amino]-2,3-dihydro-1H-pyrano[3,2-f]quinoline-8-carbonitrile (400 mg, 1.07 mmol) in t-butanol (40 mL), potassium hydroxide (800 mg, 14.3 mmol) was added at room temperature and the resulting mixture was stirred at 90° C. for 2 hour. Upon the completion of the reaction, aqueous sodium chloride solution was added to the reaction solution, and it was extracted with ethyl acetate and the resulting organic phase was dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=1/1) and recrystallized from hexane-ethyl acetate to obtain the aimed product (yield: 54%).

Workup

additionwas added to the reaction solution, and it
extractionwas extracted with ethyl acetate
dry with materialthe resulting organic phase was dried over anhydrous magnesium sulfate
distillationAfter distilling off the solvent
customthe residue was purified by column chromatography (hexane/ethyl acetate=1/1)
customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record: ord-5d7193a26c9643db8acd2d717e5c16e0
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652008B2

Reaction notes

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