Sodium Hydroxide → HCID 22247343, compound

HRID 1107978Notes

Reaction equation

[CH2:1]([N:9]1[C:18]2[C:13](=[C:14]([CH3:33])[C:15]([CH2:27][C:28]([O:30]CC)=[O:29])=[C:16]([CH3:26])[C:17]=2[NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:12][CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+]>C(O)C.O>[CH2:1]([N:9]1[C:18]2[C:13](=[C:14]([CH3:33])[C:15]([CH2:27][C:28]([OH:30])=[O:29])=[C:16]([CH3:26])[C:17]=2[NH:19][C:20](=[O:25])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:12][CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: 50 °C

Procedure

N-(1-Octyl-6-ethoxycarbonylmethyl-5,7-dimethyl-1,2,3,4-tetrahydroquinolin-8-yl)-2,2-dimethylpropanamide (230 mg) was dissolved in ethanol (5 ml), and a solution of NaOH (100 mg) in water (2 ml) was added, which was followed by stirring at 50° C. for 1 hr. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was dissolved in water (50 ml) and washed with ethyl acetate (20 ml). The aqueous layer was adjusted to pH 1-2 with 2N sulfuric acid and extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 130 mg of powdery title compound.

Workup

customThe solvent of the reaction mixture was evaporated under reduced pressure
dissolutionThe residue was dissolved in water (50 ml)
washwashed with ethyl acetate (20 ml)
extractionextracted with chloroform
dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-9d9add3a73ea47368520878cc77aadf9
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063806

Reaction notes

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