Pyridine → HCID 13535929, compound

HRID 1583804Notes

Reaction equation

HRID 1583804 reaction equation
[Na].Br[C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([N+:15]([O-:17])=[O:16])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.N1C=CC=CC=1.[F:24][C:25]([F:29])([F:28])[CH2:26][OH:27]>>[CH3:14][O:13][C:12]1[C:3]([O:27][CH2:26][C:25]([F:29])([F:28])[F:24])=[C:4]2[C:9](=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 1049PyridineHCID 64092,2,2-TrifluoroethanolHCID 94809Quinoline, 5-bromo-6-methoxy-8-nitro-HCID 5360545Sodium

Product 1

HCID 13535929HCID 13535929, compound

Procedure

To a solution of 0.5 g (0.02 g atom) of sodium in 30 ml of 2,2,2-trifluoroethanol were added 5.6 g (0.02 mole) of 5-bromo-6-methoxy-8-nitroquinoline and 7 ml of pyridine. The mixture was heated under reflux for 158 hr and filtered to remove 1.3 g of starting material. The filtrate was concentrated to 50 ml, diluted with diethyl ether, washed with water and dried (potassium carbonate). Solvent removal left a tan crystalline powder, mp 109°-115° which was extracted with benzene. (A trace of insoluble red crystals was discarded.) The benzene solution was concentrated and the resulting residue was crystallized from diethyl ether-petroleum ether (20°-40°) (5:1) to give 0.4 g of pale tan crystals of 6-methoxy-8-nitro-5-(2,2,2-trifluoroethoxy)quinoline, mp 117°-119°. Concentration of the mother liquor provided an additional 2 g of product, mp 100°-111°. Crystallization of the first fraction from diethyl ether and vacuum drying, overnight, at 60°, gave the analytical sample, mp 120°-121°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 158 hr
  3. filtrationfiltered
  4. customto remove 1.3 g of starting material
  5. concentrationThe filtrate was concentrated to 50 ml
  6. additiondiluted with diethyl ether
  7. washwashed with water
  8. dry with materialdried (potassium carbonate)
  9. customSolvent removal
  10. waitleft a tan crystalline powder, mp 109°-115° which
  11. extractionwas extracted with benzene
  12. concentration) The benzene solution was concentrated
  13. customthe resulting residue was crystallized from diethyl ether-petroleum ether (20°-40°) (5:1)

Sources & evidence

ORD record
ord-5b7bf8d978dc4403baa2785eccf19d1a
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

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