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

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

Reactant 3

HCID 313Hydrochloric Acid

HCID 6451240Aluminum(III) Chloride

HCID 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

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

Sources & evidence

ORD record: ord-6f03eb6fb6064ba79ecdc42a171ff5e8
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315462B2

Reaction notes

Loading…