Pyridine → HCID 10493059, compound

HRID 1901472Notes

Reaction equation

HRID 1901472 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([CH3:15])=[C:8]2[C:3]=1[C:4](=O)[CH2:5][CH:6]=[N:7]2.P(Br)(Br)([Br:19])=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:19][C:4]1[C:3]2[C:8](=[C:9]([CH3:15])[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=2[CH3:1])[N:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24613Phosphorus oxybromideHCID 70275766HCID 70275766, compound

Product 1

HCID 10493059HCID 10493059, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5,8-dimethyl-6-nitro-4-quinolone (7.12 g, 32.7 mmol), phosphorus oxybromide (7.47 g, 26.12 mmol), pyridine (5.3 mL), and toluene (90 mL) is heated at 90° C. for 6 hours. The mixture is filtered hot, and the solid is washed with water and methylene chloride. The filtrate is extracted with methylene chloride (3×100 mL), and the combined organic layers are dried (sodium sulfate) and evaporated to afford 4-bromo-5,8-dimethyl-6-nitroquinoline.

Workup

  1. filtrationThe mixture is filtered hot
  2. washthe solid is washed with water and methylene chloride
  3. extractionThe filtrate is extracted with methylene chloride (3×100 mL)
  4. dry with materialthe combined organic layers are dried (sodium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-285617aa0b2d44938af71fe1a72744c9
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

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