Pyridine → HCID 619014, compound

HRID 1863110Notes

Reaction equation

HRID 1863110 reaction equation
Cl.[CH3:2][NH:3][CH3:4].Br[C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([N+:18]([O-:20])=[O:19])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2.N1C=CC=CC=1>O.C([O-])(O)=O.[Na+]>[CH3:2][N:3]([CH3:4])[C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([N+:18]([O-:20])=[O:19])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 10473Dimethylamine, hydrochlorideHCID 94809Quinoline, 5-bromo-6-methoxy-8-nitro-

Product 1

HCID 619014HCID 619014, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 962WaterSolvent

Procedure

A solution of 18 g (0.22 mole) of dimethylamine hydrochloride in 50 ml of warm water was added to a stirred mixture of 30 g (0.11 mole) of 5-bromo-6-methoxy-8-nitroquinoline--Example 13A--30 g of NaHCO3 and 180 ml of pyridine. The mixture was heated under reflux for 30 hr, allowed to cool and filtered. The filtered solid was washed with acetone and the combined filtrate and washings were slowly diluted with water to 4 l. Unreacted 5-bromo compound separated first followed by product. Crystallization from methanol gave 4.9 g of 5-dimethylamino-6-methoxy-8-nitroquinoline (20% yield) as orange crystals which melted 79°-80°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 hr
  3. temperatureto cool
  4. filtrationfiltered
  5. washThe filtered solid was washed with acetone
  6. additionthe combined filtrate and washings were slowly diluted with water to 4 l
  7. customUnreacted 5-bromo compound separated first
  8. customCrystallization from methanol

Sources & evidence

ORD record
ord-fb63052873ab44adb1b8f2afc9d76246
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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