Aluminum(III) Chloride → 6-Carboxy-8-methylcarbostyril

HRID 232703

Reaction equation

HRID 232703 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=1[CH3:25])(=[O:14])[CH:6]=[CH:7]C1C=CC=CC=1>ClC1C=CC=CC=1>[C:20]([C:19]1[CH:23]=[C:24]2[C:16](=[C:17]([CH3:25])[CH:18]=1)[NH:15][C:5](=[O:14])[CH:6]=[CH:7]2)([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 538459644-Cinnamoylamino-3-methylbenzoic acid

Product 1

HCID 233590966-Carboxy-8-methylcarbostyrilYield 49.8%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
90 °C

Procedure

7.1 g of aluminum chloride was added to a solution of 2.5 g of 4-cinnamoylamino-3-methylbenzoic acid in 12.5 ml of chlorobenzene. The mixture was stirred at 90° C. for 1 hour to give rise to a reaction. The reaction mixture was poured into ice water. The resulting precipitate was collected by filtration and dispersed in 70 ml of ethanol and 70 ml of water. The dispersion was made alkaline with a 30% aqueous sodium hydroxide solution and then treated with active carbon. The resulting material was made acidic with concentrated hydrochloric acid. The resulting precipitate was collected by filtration and then washed with hot ethanol to obtain 0.9 g of 6-carboxy-8-methylcarbostyril as a light brown powder.

Workup

  1. customto give rise
  2. customto a reaction
  3. filtrationThe resulting precipitate was collected by filtration
  4. additiondispersed in 70 ml of ethanol
  5. additiontreated with active carbon
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with hot ethanol

Sources & evidence

ORD record
ord-c727b096a0914ce581ea03480a96ad4d
Source dataset
uspto-grants-1997_01
Patent number
US05591751

Linked notes

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