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

HRID 55847Notes

Reaction equation

HRID 55847 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-751a4c22cc7c4afb9844290a8c529461
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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