Ethanol → N-(3-methoxy-2-hydroxypropyl)-6-benzyloxy-2-naphthylamine

HRID 1646962Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.0 g of 3-(6-benzyloxy-2-naphthyl)-5-methoxymethyl-2-oxazolidone, 20 ml of ethanol, 4 ml of water and 1.08 g of potassium hydroxide is stirred at 100° C. for one hour. The reaction mixture is evaporated under reduced pressure to remove the ethanol. The residue is extracted with ethyl acetate, and the extract is washed with water, dried and evaporated under reduced pressure to remove the solvent. The residue is recrystallized from ethyl acetate-hexane to give 1.64 g of N-(3-methoxy-2-hydroxypropyl)-6-benzyloxy-2-naphthylamine as colorless needles.

Workup

customThe reaction mixture is evaporated under reduced pressure
customto remove the ethanol
extractionThe residue is extracted with ethyl acetate
washthe extract is washed with water
customdried
customevaporated under reduced pressure
customto remove the solvent
customThe residue is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-19470cde384c49d9b9167cceb5a62eaf
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05182296

Reaction notes

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