1-Bromo-4-methylnaphthalene → HCID 20363803, compound

HRID 1679136Notes

Reaction equation

HRID 1679136 reaction equation
C([Li])CCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[CH:9][CH:8]=1.[CH3:18][C:19]1([CH3:36])[CH2:28][C:27](=O)[C:26]2[C:21](=[CH:22][C:23]([O:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[CH:24][CH:25]=2)[O:20]1>O1CCCC1.CCOCC>[CH3:18][C:19]1([CH3:36])[CH:28]=[C:27]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[CH:9][CH:8]=2)[C:26]2[C:21](=[CH:22][C:23]([O:30][CH2:31][CH2:32][N:33]([CH3:34])[CH3:35])=[CH:24][CH:25]=2)[O:20]1

Participants

6

Reactant 3

HCID 811121-Bromo-4-methylnaphthaleneHCID 205705632,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-chromanoneHCID 178418339Butyllithium

Product 1

HCID 20363803HCID 20363803, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of butyl lithium (12.5 ml, 0.03 mole, 2.4M solution in hexane) was added dropwise over 20 minutes a solution of 1-bromo-4-methylnaphthalene (6.63 g, 0.03 mole) in dry tetrahydrofuran (10 ml), the reaction mixture being cooled throughout by a water bath. After being stirred at ambient temperature for 15 minutes the resulting suspension was treated with a solution of 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4-chromanone (4.0 g, ~0.015 mole) in dry tetrahydrofuran (15 ml), the precipitate almost immediately dissolving to give a golden yellow solution. The resulting solution was stirred under reflux for 5 hours, then left overnight at ambient temperature, stirred under reflux for a further 7 hours and again left overnight at ambient temperature. After work up with acid, by an analogous process to that described in Example 1 and chromatography on alumina in 8% ether - 92% petroleum ether (b.p. 60°-80°) the title compound was obtained as a colourless oil (0.65 g, 11%). Its hydrochloride salt was m.p. 215°-216.5° C.

Workup

  1. temperaturethe reaction mixture being cooled throughout by a water bath
  2. dissolutionthe precipitate almost immediately dissolving
  3. customto give a golden yellow solution
  4. stirringThe resulting solution was stirred
  5. temperatureunder reflux for 5 hours
  6. waitleft overnight at ambient temperature
  7. stirringstirred
  8. temperatureunder reflux for a further 7 hours and again left overnight at ambient temperature

Sources & evidence

ORD record
ord-4f2e38f27a284716be639f85637b8291
Source dataset
uspto-grants-1978_03
Patent number
US04079066

Reaction notes

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