Hexane → Ethyl 4-[2-(1,2,3,4-tetrahydro-5-naphthyloxy)ethylamino]benzoate

HRID 443651Notes

Reaction equation

HRID 443651 reaction equation
[H-].[Na+].CCCCCC.[CH2:9]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:19])[C:13]=2[CH2:12][CH2:11][CH2:10]1.Br[CH2:21][CH2:22][NH:23][C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1>C(COC)OC>[CH2:9]1[C:18]2[C:13](=[C:14]([O:19][CH2:21][CH2:22][NH:23][C:24]3[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 23468291Ethyl 4-(2-bromoethylamino)benzoate

Product 1

HCID 23468308Ethyl 4-[2-(1,2,3,4-tetrahydro-5-naphthyloxy)ethylamino]benzoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a slurry of 2.3 g. of 57% sodium hydride-in-oil (previously washed free of oil with hexane) in 20 ml. of dimethoxyethane is added 7.4 g. of 1,2,3,4-tetrahydro-5-naphthol in 20 ml. of dimethoxyethane and then 13.6 g. of ethyl 4-(2-bromoethylamino)benzoate. After refluxing for 6 hours and dilution with 300 ml. of water, the solid is collected and recrystallized from acetonitrile, m.p. 133°-135° C.

Workup

  1. temperatureAfter refluxing for 6 hours
  2. customof water, the solid is collected
  3. customrecrystallized from acetonitrile, m.p. 133°-135° C.

Sources & evidence

ORD record
ord-0f9d53abd0f442ee8124995903aa692c
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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