Hydrochloric Acid → 8-Fluoro-6-hydroxy-3,4-dihydroquinolin-2(1H)-one

HRID 2280503Notes

Reaction equation

HRID 2280503 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[F:14])=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].Cl>>[F:14][C:8]1[CH:9]=[C:10]([OH:13])[CH:11]=[C:12]2[C:7]=1[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 669800713-chloro-N-(2-fluoro-4-hydroxyphenyl)propanamide

Product 1

HCID 103750488-Fluoro-6-hydroxy-3,4-dihydroquinolin-2(1H)-one

Conditions

Temperature
160 °C

Procedure

3-Chloro-N-(2-fluoro-4-hydroxyphenyl)propanamide (2.1 g) was mixed with anhydrous AlCl3 (7 g) and heated at 160° C. overnight. The resultant mixture was treated with 1N HCl and extracted with EtOAc. After isolation of the organic layer and removal of solvents under reduced pressure, the desired crude product (1.8 g) was collected as light brown solids.

Workup

  1. extractionextracted with EtOAc
  2. customAfter isolation of the organic layer and removal of solvents under reduced pressure
  3. customthe desired crude product (1.8 g) was collected as light brown solids

Sources & evidence

ORD record
ord-1dc77d2b00d14028b67f1f5f13ce41e6
Source dataset
uspto-grants-2015_09
Patent number
US09139528B2

Reaction notes

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