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Water → 2,2-dibutyl-3,4-dihydro-5-(2-quinolylmethoxy)-1(2H)-naphthalenone

HRID 727814
Notes
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Reaction equation

HRID 727814 reaction equation
[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:15])[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].Cl[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 10659962HCID 10659962, compound

Product 1

HCID 105497902,2-dibutyl-3,4-dihydro-5-(2-quinolylmethoxy)-1(2H)-naphthalenoneYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,2-dibutyl-3,4-dihydro-5-hydroxy-(2H)-naphthalenone (2.643 g), 2-chloromethylquinoline (1.7 g), and potassium carbonate (1.67 g) in N,N-dimethylformamide (16 ml) was stirred at 80° C. for 4 hours. The cooled mixture was poured into water. The separated oil was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried, and concentrated in vacuo. The crude product was chromatographed on silica gel using 25% ethyl acetate in n-hexane as eluent to yield 2,2-dibutyl-3,4-dihydro-5-(2-quinolylmethoxy)-1(2H)-naphthalenone (3.09 g) as a pale yellow syrup.

Workup

  1. extractionThe separated oil was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed on silica gel using 25% ethyl acetate in n-hexane as eluent

Sources & evidence

ORD record
ord-7d1c6828d20b464a8b7aad5a7dc2222b
Source dataset
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05045548

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes