Aluminum(III) Chloride → 3-(3-Hydroxyphenyl)quinolin-7-ol

HRID 1035643Notes

Reaction equation

HRID 1035643 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Cl-].[Cl-].[Cl-].[Al+3]>>[OH:19][C:15]1[CH:14]=[C:13]([C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[C:3]([OH:2])[CH:12]=3)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 248274327-Methoxy-3-(3-methoxyphenyl)quinoline

Product 1

HCID 1357833653-(3-Hydroxyphenyl)quinolin-7-olYield 76%

Procedure

The compound is prepared by reaction of 7-methoxy-3-(3-methoxyphenyl)-quinoline (108 mg, 0.40 mmol, 1 eq) with aluminum trichloride (433 mg, 3.26 mmol, 8 eq) according to method F. Purification by column chromatography with dichloromethane/methanol 95/5 as the eluent yields the desired product in a yield of 76%, 73 mg.

Workup

  1. customPurification by column chromatography with dichloromethane/methanol 95/5 as the eluent

Sources & evidence

ORD record
ord-2884463afbd0406f888a34da25eed644
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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