Ammonium → 2-Chloro-4-methyl-7-aminoquinoline

HRID 1005673Notes

Reaction equation

HRID 1005673 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[C:9](OCC)(=O)[CH2:10][C:11]([CH3:13])=O.P(Cl)(Cl)([Cl:20])=O.[NH4+]>>[NH2:7][C:3]1[CH:2]=[C:1]2[C:6]([C:11]([CH3:13])=[CH:10][C:9]([Cl:20])=[N:8]2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 223AmmoniumHCID 7935M-PhenylenediamineHCID 8868Ethyl AcetoacetateHCID 24813Phosphorus oxychloride

Product 1

HCID 2300872-Chloro-4-methyl-7-aminoquinoline

Procedure

To 27 g (251 mmol) of m-phenylenediamine was added 32 ml (251 mmol) of ethyl acetoacetate, followed by stirring at 200 degrees for 1 hour. After standing to cool, the crystals were washed with hexane. To 9.5 g (54 mmol) of the crystals was added 15 ml of phosphorus oxychloride, followed by heating under reflux for 2 hours. After standing to cool, the reaction mixture was poured onto ice-water and basified with a saturated ammonium aqueous solution. The resulting crystals were collected by filtration and washed with water. The crystals were washed with methanol and the filtrate was evaporated, to give 4.85 g of the title compound.

Workup

  1. temperatureto cool
  2. washthe crystals were washed with hexane
  3. temperatureby heating
  4. temperatureunder reflux for 2 hours
  5. temperatureto cool
  6. additionthe reaction mixture was poured onto ice-water
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with water
  9. washThe crystals were washed with methanol
  10. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-40b77da48ea1497fb46b82ee05149789
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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