Ammonia → 2,6-Dimethyl-5-nitroquinoline

HRID 2215472

Reaction equation

HRID 2215472 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1.S(=O)(=O)(O)O.[N+:18]([O-])([O-:20])=[O:19].[K+].N>>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[C:8]=2[N+:18]([O-:20])=[O:19])[N:3]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric Acid2×HCID 134142,6-DimethylquinolineHCID 24434Potassium Nitrate

Product 1

HCID 7665652,6-Dimethyl-5-nitroquinoline

Procedure

3 g (19.08 mmol) of 2,6-dimethylquinoline is introduced into 15 ml of concentrated sulfuric acid at 10° C. After one-half hour, a solution of 2.03 g of potassium nitrate in 11.4 concentrated sulfuric acid is added in drops, specifically so that the temperature remains between 5° and 15° C. The batch is stirred for one more hour and then poured onto ice water. It is made ammonia-alkaline, and the deposited precipitate is suctioned off. After washing with water, the crude product is dissolved in ethyl acetate and shaken from water. The organic phase is treated as usual. After the solvent is spun off, 3.69 g (95.6%) of the desired compound remains, which is used in the reduction without further purification.

Workup

  1. waitAfter one-half hour
  2. customremains between 5° and 15° C
  3. additionpoured onto ice water
  4. washAfter washing with water
  5. dissolutionthe crude product is dissolved in ethyl acetate
  6. stirringshaken from water
  7. additionThe organic phase is treated as usual
  8. customwhich is used in the reduction without further purification

Sources & evidence

ORD record
ord-97519779343f4c27b1dd940fe5f36a6b
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Linked notes

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