Sulfuric Acid → 4-Chloroquinoline-7-carboxylic acid

HRID 964998Notes

Reaction equation

HRID 964998 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](F)(F)F)=[CH:9][CH:10]=2)N=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:17].[OH2:21].[NH3:22]>>[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2]([Cl:1])=[CH:3][CH:4]=[N:22]2)=[CH:10][CH:9]=1)([OH:17])=[O:21]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 12896473Azane;hydrate

Product 1

HCID 217084474-Chloroquinoline-7-carboxylic acidYield 74%

Conditions

Temperature
100 °C

Procedure

Commercially available 4-chloro-7-(trifluoromethyl)-quinoline (8 g, 0.035 mol) was added under ice cooling with 30% fuming sulfuric acid (35 ml) and stirred at 100° C. for 5 hours. After allowing to cool to room temperature, the reactant was poured into ice water and made basic enough with excess concentrated ammonia water, and insoluble materials were filtered off. The filtrate was adjusted by 2N hydrochloric acid to pH 3-4. The resulting jellied precipitate was collected by filtration, washed with ethanol (50 ml) and dried under reduced pressure over phosphorus pentoxide to obtain 5.4 g (74%) of 7-carboxy-4-chloroquinoline.

Workup

  1. temperatureto cool to room temperature
  2. filtrationwere filtered off
  3. filtrationwas collected by filtration
  4. washwashed with ethanol (50 ml)
  5. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-f64f25193dfd4810aa289b46f9377a4d
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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