Propylene Oxide → HCID 13535931, compound

HRID 1583806Notes

Reaction equation

HRID 1583806 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][CH3:22].C(N(CC)CC)C.C1OC1C>CN(C)P(=O)(N(C)C)N(C)C>[CH2:17]([O: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)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 6378Propylene Oxide2×HCID 81011-BromohexaneHCID 8471TriethylamineHCID 1353992885323-58-0

Product 1

HCID 13535931HCID 13535931, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A stirred mixture of 5-hydroxy-6-methoxy-8-nitroquinoline (22 g, 0.1 mole), n-hexyl bromide (18.5 g, 0.11 mole), triethylamine (1 g) and hexamethylphosphoric triamide (16 ml) was maintained at a bath temperature of 120°-130° while 10 g of propylene oxide was added during 0.5 hr. The mixture was heated at a bath temperature of 130°-145° for 3 hr and 5 more grams of propylene oxide was added. After 8 hr at 110°-120°, a low-boiling fraction was distilled off at 100° (1 atm) and the residue was cooled and poured into 3 liters of ice water. The resulting dull red solid was filtered and extracted with diethyl ether (2.5 g of 5-hydroxy compound was recovered as a diethyl ether-insoluble red solid). The ether extract was washed with dilute sodium hydroxide and water, dried (sodium sulfate) and concentrated to leave a thick oil. Trituration with petroleum ether (bp 20°-40°) gave 19.5 g (65%) of the required 5-hexoxy-quinoline derivative as a tan solid, mp 46°-49°. Crystallization from aqueous methanol (carbon) provided an analytical sample as yellow needles, mp 53°-55°.

Workup

  1. additionwas added during 0.5 hr
  2. temperatureThe mixture was heated at a bath temperature of 130°-145° for 3 hr
  3. distillationa low-boiling fraction was distilled off at 100° (1 atm)
  4. temperaturethe residue was cooled
  5. additionpoured into 3 liters of ice water
  6. filtrationThe resulting dull red solid was filtered
  7. extractionextracted with diethyl ether (2.5 g of 5-hydroxy compound
  8. customwas recovered as a diethyl ether-insoluble red solid)
  9. extractionThe ether extract
  10. washwas washed with dilute sodium hydroxide and water
  11. dry with materialdried (sodium sulfate)
  12. concentrationconcentrated
  13. customto leave a thick oil

Sources & evidence

ORD record
ord-5ba0fe46cc4f485a9b128ca39f760ef5
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

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