Propylene Oxide → HCID 53923883, compound

HRID 1030194Notes

Reaction equation

HRID 1030194 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[S:25][CH:26]=[CH:27][CH:28]=1.CN(P(N(C)C)(N(C)C)=O)C.C1OC1C>CCN(CC)CC>[CH3:13][O:12][C:11]1[C:2]([O:1][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[C:3]2[C:8](=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=1)[N:7]=[CH:6][CH:5]=[C:4]2[CH3:17]

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 12679HexamethylphosphoramideHCID 22115197HCID 22115197, compoundHCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline

Product 1

HCID 53923883HCID 53923883, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mechanically stirred mixture of 5-hydroxy-6-methoxy-4-methyl-8-nitroquinoline (WRAIR; 5.67 g, 0.023 mol), 1-bromo-5-(2-thienyl) pentane from previous step a (5.32 g, 0.023 mol) and HMPA (40 ml), at 115°-120° C., was added dropwise, during 45 min, a solution of Et3N (5 ml) and propylene oxide (10 ml). The mixture was heated at 115°-120° C. for 5 hr, allowed to cool and extracted with a solution of pet. ether (20°-40° C.) and Et2O (1:1 v/v, 200 ml). The extract was washed with 10% NaOH solution (3×75 ml) and the combined basic washings were re-extracted with pet. ether (20°-40°) and Et2O solution (1:1 v/v, 2×100 ml). The combined organic layers were washed with H2O (2×100 ml), dried (K2CO3), and treated with carbon (Darco G-60). Solvent evaporation gave 6-methoxy-4-methyl-8-nitro-5-[5-(2-thienyl) pentoxy] quinoline as a yellow solid, 5.61 g (61%), mp 51°-54° C. This material was used without further purification.

Workup

  1. additionat 115°-120° C., was added dropwise, during 45 min
  2. temperatureThe mixture was heated at 115°-120° C. for 5 hr
  3. temperatureto cool
  4. extractionextracted with a solution of pet. ether (20°-40° C.) and Et2O (1:1 v/v, 200 ml)
  5. washThe extract was washed with 10% NaOH solution (3×75 ml)
  6. extractionthe combined basic washings were re-extracted with pet. ether (20°-40°) and Et2O solution (1:1 v/v, 2×100 ml)
  7. washThe combined organic layers were washed with H2O (2×100 ml)
  8. dry with materialdried (K2CO3)
  9. additiontreated with carbon (Darco G-60)
  10. customSolvent evaporation

Sources & evidence

ORD record
ord-e7cbb93a4b5a44438bfaa24d6a55ad1b
Source dataset
uspto-grants-1992_04
Patent number
US05104885

Reaction notes

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