Chlorobenzene → 3,8-Dimethyl-5-hydroxycarbostyril

HRID 1900807Notes

Reaction equation

HRID 1900807 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:21])=[C:7]([NH:9][C:10](=[O:20])[C:11]([CH3:19])=[CH:12]C2C=CC=CC=2)[CH:8]=1.[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1>CCCCCC>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:21])=[C:7]2[C:8]=1[CH:19]=[C:11]([CH3:12])[C:10](=[O:20])[NH:9]2

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 54285619N-(5-Methoxy-2-methylphenyl)alpha-methylcinnamamide

Product 1

HCID 233696243,8-Dimethyl-5-hydroxycarbostyrilYield 85.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
125 °C

Procedure

N-(5-Methoxy-2-methylphenyl)α-methylcinnamamide (21.3 g, 75.8 mmol) and aluminum chloride (50.4 g, 378 mmol) were combined with chlorobenzene (158 ml), and heated in a bath at 125° C. for 45 minutes while stirring. After cooling, the mixture was poured into ice-water, to which hexane was added. Precipitated crystals were collected by filtration, and dissolved in chloroform-methanol (4:1). After drying and condensing, the resultant residue was washed with chloroform to obtain 12.22 g of the title compound as pale brown crystals (85.3%).

Workup

  1. temperatureAfter cooling
  2. additionwas added
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. dissolutiondissolved in chloroform-methanol (4:1)
  6. customAfter drying
  7. customcondensing
  8. washthe resultant residue was washed with chloroform

Sources & evidence

ORD record
ord-985f4521d72045a2998b995cc89f35cb
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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