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

HRID 1729322
Notes
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Reaction equation

HRID 1729322 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 1317177253-(6-Benzyloxy-2-naphthyl)-5-methoxymethyl-2-oxazolidone

Product 1

HCID 19012494N-(3-methoxy-2-hydroxypropyl)-6-benzyloxy-2-naphthylamineYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customto remove the ethanol
  3. extractionThe residue is extracted with ethyl acetate
  4. washthe extract is washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is recrystallized from ethyl acetate - hexane

Sources & evidence

ORD record
ord-7c269d4b45724c90aa48e5eef4302e18
Source dataset
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05332754

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes