Propylene Oxide → HCID 19822136, compound

HRID 1030197Notes

Reaction equation

HRID 1030197 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.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1.CN(P(N(C)C)(N(C)C)=O)C.C1OC1C>CCN(CC)CC>[O:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][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

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 12679HexamethylphosphoramideHCID 10398435HCID 10398435, compoundHCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline

Product 1

HCID 19822136HCID 19822136, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mechanically stirred mixture of 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline (WRAIR, 4.00 g, 0.017 mol), 1-bromo-5-(2-furyl) pentane (3.65 g, 0.017 mol) and HMPA (25 ml), at 105°-110° C., was added dropwise, during 60 min, a solution of Et3N(3.5 ml) and propylene oxide (6.5 ml). The mixture was heated at 105°-110° C. for 2 hr, allowed to cool and extracted with a solution of pet. ether (20°-40° C.) and Et2O (1:1 v/v, 200 ml), leaving behind a black residue. The organic layer was washed with 10% NaOH solution (3×50 ml). The combined basic wash solutions were re-extracted with a pet. ether (20°-40° C.)-Et2O solution (1:1 v/v, 2×75 ml) and the combined organic layers were washed with H2O (2×50 ml), dried (Na2SO4), treated with Darco, filtered and concentrated to give 5-[5-(2-furyl) pentoxy]-6-methoxy-4-methyl-8-nitroquinoline as a yellow solid, 2.5 g (40%) mp. 47°-49° C. This material was used without further purification.

Workup

  1. additionat 105°-110° C., was added dropwise, during 60 min
  2. temperatureThe mixture was heated at 105°-110° C. for 2 hr
  3. temperatureto cool
  4. extractionextracted with a solution of pet. ether (20°-40° C.) and Et2O (1:1 v/v, 200 ml)
  5. customleaving behind a black residue
  6. washThe organic layer was washed with 10% NaOH solution (3×50 ml)
  7. extractionThe combined basic wash solutions were re-extracted with a pet. ether (20°-40° C.)-Et2O solution (1:1 v/v, 2×75 ml)
  8. washthe combined organic layers were washed with H2O (2×50 ml)
  9. dry with materialdried (Na2SO4)
  10. additiontreated with Darco
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-44755d4755e34147851a4f0e96dff333
Source dataset
uspto-grants-1992_04
Patent number
US05104885

Reaction notes

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