Aluminum(III) Chloride → HCID 23369592, compound

HRID 1900859Notes

Reaction equation

HRID 1900859 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[NH:10][C:11](=[O:16])[CH:12]=[C:13]([CH3:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=C(Cl)C=1>[CH3:14][C:13]1([CH3:15])[C:4]2[C:3](=[CH:2][CH:7]=[CH:6][C:5]=2[OH:8])[NH:10][C:11](=[O:16])[CH2:12]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 23369707HCID 23369707, compound

Product 1

HCID 23369592HCID 23369592, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 109431,3-DichlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

N-(2-Brom-5-methoxyphenyl)-3,3-dimethylacrylamide (530 mg, 1.87 mmol) was dissolved in m-dichlorobenzene (10 ml). To the resultant solution, aluminum chloride (1.24 g, 9.33 mmol) was added, and the mixture was stirred at 120° C. for 40 minutes. The reaction mixture was poured into ice-water, followed by extracting with chloroform-methanol (10:1), and drying. Subsequently, the residue was subjected to silica gel column chromatography (developer=chloroform-methanol =30:1). From the first eluate, 152 mg of 4,4-dimethyl-5-hydroxy-3,4-dihydrocarbostyril (152 mg, 42.5%) was obtained as pale yellow needles. From the second eluate, 4,4-dimethyl-7-hydroxy-3,4-dihydrocarbostyril (63 mg, 17.6%) was obtained as pale yellow needles.

Workup

  1. extractionby extracting with chloroform-methanol (10:1)
  2. customdrying

Sources & evidence

ORD record
ord-bfdfca7e6641482083ea853b64fddf51
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…