3-Chloro-2-methyl-1-propene → HCID 86733866, compound

HRID 2397917Notes

Reaction equation

HRID 2397917 reaction equation
[CH3:1][C:2]1([CH3:17])[C:11]2[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=2[CH2:9][C@H:8]2[C@@H:3]1[CH2:4][CH2:5][CH2:6][NH:7]2.C(=O)(O)[O-].[Na+].[CH3:23][C:24](=[CH2:27])[CH2:25]Cl>CN(C)C=O>[CH3:25][C:24](=[CH2:23])[CH2:27][N:7]1[C@@H:8]2[C@@H:3]([C:2]([CH3:17])([CH3:1])[C:11]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=3[CH2:9]2)[CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 516892Sodium BicarbonateHCID 86733867HCID 86733867, compound

Product 1

HCID 86733866HCID 86733866, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.92 g. of cis-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[g]-quinolin-7-ol, 2.52 g. of sodium bicarbonate, 2.98 g. of 2-methyl-2-propenyl chloride, and 60 ml. of N,N-dimethylformamide was stirred and refluxed for one hour. The reaction mixture was worked up in a manner similar to that described above in Example 11 to yield crude cis-1,2,3,4,4a,5,10,10a-octahydro-1-(2-methyl-2-propenyl)-5,5-dimethylbenzo[g]quinolin-7-ol. A 1.7 g. portion of the partially purified base was chromatographed on 170 g. of alumina (6% water) using diethyl ether as eluant, and the resulting syrupy product (1.3 g.) was recrystallized from hexane to yield 1.0 g. of the pure base as an off-white solid melting at 129°-131° C.

Workup

  1. additionA mixture of 6.92 g
  2. temperaturerefluxed for one hour

Sources & evidence

ORD record
ord-1f936dade07347ab96cf0987cca09c3d
Source dataset
uspto-grants-1977_05
Patent number
US04022792

Reaction notes

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