Propylene Oxide → HCID 13535933, compound

HRID 1583808Notes

Reaction equation

HRID 1583808 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[C:4]([CH3:17])=[CH:5][CH:6]=[N:7]2.[CH2:18](Br)[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>[CH2:18]([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[C:4]([CH3:17])=[CH:5][CH:6]=[N:7]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 6378Propylene Oxide2×HCID 123691-BromoheptaneHCID 12679HexamethylphosphoramideHCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline

Product 1

HCID 13535933HCID 13535933, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A stirred mixture of 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline [from Example 7B]--14.0 g, 0.06 mole - n-heptyl bromide (7.5 g, 0.045 mole) and hexamethylphosphoric triamide (12 ml) was heated at 120°, under N2, while a mixture of triethylamine (1 ml) and propylene oxide (6 ml) was added in small portions during 6 hr. Additional propylene oxide (4 ml) was added during 4 hr and the mixture was cooled and filtered and the dull red solid was washed with acetone to return 7.5 g of starting material. The combined filtrate and washings were diluted with water and the resulting solid was extracted with diethyl ether. The extract was washed with 5% sodium hydroxide and water, treated with carbon, dried (sodium sulfate) and evaporated to dryness. Trituration of the dark brown residual oil with petroleum ether (20°-40°) produced a tan solid which was extracted with additional petroleum ether (700 ml). Concentration of the extract to 300 ml and cooling in a Dry-Ice bath gave 7 g (52%) of 5-heptoxy-6-methoxy-4-methyl-8-nitroquinoline as a pale yellow solid, mp 52°-55°. Recrystallization from petroleum ether (20°-40°) provided the analytical sample as glistening pale yellow crystals, mp 56°-57°.

Workup

  1. additionwas added in small portions during 6 hr
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. washthe dull red solid was washed with acetone
  5. additionThe combined filtrate and washings were diluted with water
  6. extractionthe resulting solid was extracted with diethyl ether
  7. washThe extract was washed with 5% sodium hydroxide and water
  8. additiontreated with carbon
  9. dry with materialdried (sodium sulfate)
  10. customevaporated to dryness
  11. customTrituration of the dark brown residual oil with petroleum ether (20°-40°) produced a tan solid which
  12. extractionwas extracted with additional petroleum ether (700 ml)
  13. extractionConcentration of the extract to 300 ml
  14. temperaturecooling in a Dry-Ice bath

Sources & evidence

ORD record
ord-6894f0e8a7ac4525990e48c865fff838
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

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