Hydrochloric Acid → HCID 58368502, compound

HRID 1192577Notes

Reaction equation

HRID 1192577 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl-].[Cl-].[Cl-].[Al+3].[C:17](Cl)(=[O:19])[CH3:18].Cl.[OH-].[Na+]>O>[F:1][C:2]1[CH:11]=[C:10]([C:17](=[O:19])[CH3:18])[C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 2179075-Fluoro-8-quinolinolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 58368502HCID 58368502, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A mixture of 5-fluoroquinolin-8-ol (15.0 g, 91.9 mmol, from TCI), aluminum trichloride (50.00 g, 375.0 mmol), and acetyl chloride (30.2 mL, 425 mmol) was stirred at 0° C. for 4 hours, then heated at 130° C. for 12 hours, cooled, and decomposed with water (98 mL) (with external ice-cooling when necessary) and conc. hydrogen chloride in water (33 mL). The precipitate was filtered, and dried under reduced pressure. The solid obtained was then dissolved in 100 mL of water. The mixture was cooled with an ice bath and its pH was adjusted to 4 with slow addition of 20% NaOH. The suspension was filtered, washed with water and air dried to give the desired product (18.9 g, 100%). LCMS calculated for C11H9FNO2 (M+H)+: m/z =206.1; Found: 206.0.

Workup

  1. temperatureheated at 130° C. for 12 hours
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. customdried under reduced pressure
  5. customThe solid obtained
  6. temperatureThe mixture was cooled with an ice bath
  7. filtrationThe suspension was filtered
  8. washwashed with water and air
  9. customdried

Sources & evidence

ORD record
ord-9f20a12e926444c59a04aa9be1ec4a32
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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