Nitric Acid → 4,7-Dichloro-8-nitroquinoline

HRID 513419Notes

Reaction equation

HRID 513419 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[N:14]=[CH:13][CH:12]=1>>[Cl:10][C:11]1[C:20]2[C:15](=[C:16]([N+:1]([O-:4])=[O:2])[C:17]([Cl:21])=[CH:18][CH:19]=2)[N:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 68664,7-Dichloroquinoline

Product 1

HCID 2201774,7-Dichloro-8-nitroquinolineYield 94%

Procedure

Fuming nitric acid (8 ml) and concentrated sulfuric acid (16 ml) were combined cautiously at −10° C. 4,7-dichloroquinoline (5 g, 25 mmol) was added portionwise at −10° C. and after complete addition the mixture was allowed to warm to room temperature and stirring continued for 18 h. The reaction mixture was poured onto ice and the resulting solid removed by filtration washed with water (100 ml) to give the title compound (5.7 g, 94%).

Workup

  1. customwere combined cautiously at −10° C
  2. additionafter complete addition the mixture
  3. additionThe reaction mixture was poured onto ice
  4. customthe resulting solid removed by filtration
  5. washwashed with water (100 ml)

Sources & evidence

ORD record
ord-806822241a654a37bb2bba52504f0099
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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