1-Bromonaphthalene → HCID 20363807, compound

HRID 1679140Notes

Reaction equation

HRID 1679140 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Mg:12].[CH3:13][N:14]([CH3:29])[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24](=O)[CH2:23][CH2:22][CH2:21]2.[Cl-].[NH4+]>O1CCCC1>[C:19]1([Mg:12][Br:1])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][CH:18]=1.[C:2]1([C:24]2[C:25]3[C:20](=[CH:19][C:18]([O:17][CH2:16][CH2:15][N:14]([CH3:29])[CH3:13])=[CH:27][CH:26]=3)[CH2:21][CH2:22][CH:23]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 70011-BromonaphthaleneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 122143876-(2-Dimethylaminoethoxy)-1-tetralone

Product 2

HCID 20363807HCID 20363807, compoundYield 25.3%HCID 178418298HCID 178418298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Naphthylmagnesium bromide was prepared by the addition of 1-bromonaphthalene (9.6 g, 0.046 mole) to magnesium (1 g) in tetrahydrofuran (25 ml). 6-(2-dimethylaminoethoxy)-1-tetralone (9.8 g, 0.046 mole) in tetrahydrofuran 75 ml) was added over 1/2 hour and the reaction mixture refluxed for 2 hours. After cooling, saturated ammonium chloride solution was added and the organic layer separated. Removal of the solvent gave an oil which after chromatography on alumina, eluting with ether - light petroleum (b.p. 60°-80°) gave 1-(1-naphthyl-3,4-dihydro-6(2-dimethylaminoethoxy)naphthalene (2.0 g, 15%) as a colourless oil which was converted to the hydrochloride salt m.p. 168°-170° C.

Workup

  1. temperaturethe reaction mixture refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe organic layer separated
  4. customRemoval of the solvent
  5. customgave an oil which after chromatography on alumina
  6. washeluting with ether - light petroleum (b.p. 60°-80°)

Sources & evidence

ORD record
ord-a24110a120bf415bbdcb6779ae41919c
Source dataset
uspto-grants-1978_03
Patent number
US04079066

Reaction notes

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