Propylene Oxide → HCID 613143, compound

HRID 1583809Notes

Reaction equation

HRID 1583809 reaction equation
[OH:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CN(C)P(=O)(N(C)C)N(C)C.C1OC1C>C(N(CC)CC)C>[CH3:13][O:12][C:11]1[C:2]([O:1][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:3]2[C:8](=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=1)[N:7]=[CH:6][CH:5]=[CH:4]2

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 81401-BromooctaneHCID 12679HexamethylphosphoramideHCID 1353992885323-58-0

Product 1

HCID 613143HCID 613143, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A stirred mixture of 5-hydroxy-6-methoxy-8-nitroquinoline, (6.6 g, 0.03 mole), n-octylbromide (6.7 g, 0.035 mole) and hexamethylphosphoric triamide (10 ml) was maintained at 125°-130°, under N2, while a mixture of triethylamine (1 ml) and propylene oxide (6 ml) was added in small portions during 3 hr. The mixture was cooled and extracted with petroleum ether (bp 20°-40°) (3×100 ml). The extracts were discarded. The petroleum ether-insoluble, semi-solid residue was dissolved in 300 ml of diethyl ether and washed with water, dilute sodium hydroxide and water. The ethereal solution was dried and concentrated in vacuo to leave 8 g of pale brown solid. Crystallization from boiling petroleum ether (20°-40°) (carbon) gave 7.5 g (75%) of the 5-octoxyquinoline derivative, mp 52°-54°. An additional crystallization from petroleum ether did not change the melting point.

Workup

  1. additionwas added in small portions during 3 hr
  2. temperatureThe mixture was cooled
  3. extractionextracted with petroleum ether (bp 20°-40°) (3×100 ml)
  4. dissolutionThe petroleum ether-insoluble, semi-solid residue was dissolved in 300 ml of diethyl ether
  5. washwashed with water, dilute sodium hydroxide and water
  6. customThe ethereal solution was dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2631133c43344a1196639a83e2fd019e
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

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