Methyl Bromide → HCID 21521290, compound

HRID 918219Notes

Reaction equation

HRID 918219 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=2[OH:12])[CH2:5][CH2:4][CH2:3]1.[CH3:16][Br:17]>C(#N)C>[Br-:17].[CH3:1][N+:2]1([CH3:16])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=2[OH:12])[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6323Methyl BromideHCID 215213081,2,3,4-Tetrahydro-1-methyl-7-propyl-8-quinolinol

Product 1

HCID 21521290HCID 21521290, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a tube, one introduces 7.5 g of N-methyl-1,2,3,4-tetrahydro-7-propyl-8-hydroxyquinoline (i.e. 0.035 mole) and 4 g of methyl bromide (i.e. 0.035 mole). One adds 10 ml of acetonitrile, one seals the tube and one heats in an oil bath, at 70°C, for 90 hours. After cooling, one dries the compound that is formed, washes with anhydrous ether, and recrystallizes in boiling isopropanol (1 g of product, 2 ml of alcohol). One collects whitish crystals, which one washes again with ether, then one dries the resulting quaternary salt in a drier over sulfuric acid. One obtains 8 g of product, i.e. a yield of 735/1000.

Workup

  1. temperatureAfter cooling
  2. customone dries the compound that is formed
  3. customwashes with anhydrous ether, and recrystallizes

Sources & evidence

ORD record
ord-6b9b2b7cdbbd4ce09c2554cfeaba8796
Source dataset
uspto-grants-1976_07
Patent number
US03970454

Reaction notes

Loading…