Sodium Chloride → HCID 86617186, compound

HRID 2425344Notes

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, sodium chloride aqueous 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 with 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 with hexane-ethyl acetate

Sources & evidence

ORD record: ord-f543f846724f4561ac890ae1a838fea2
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964623B2

Reaction notes

Loading…