Water → HCID 10464809, compound

HRID 1900778Notes

Reaction equation

HRID 1900778 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:19])[CH:11]=[CH:12]C2C=CC=CC=2)=[C:5]([CH3:20])[CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1.O>CCCCCC>[OH:2][C:3]1[CH:8]=[C:7]2[C:6](=[C:5]([CH3:20])[CH:4]=1)[NH:9][C:10](=[O:19])[CH:11]=[CH:12]2

Participants

6

Reactant 4

HCID 962WaterHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 53741968HCID 53741968, compound

Product 1

HCID 10464809HCID 10464809, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
125 °C

Procedure

To N-(4-methoxy-2-methylphenyl)cinnamamide (28.33 g, 0.106M), aluminum chloride (70.5 g, 529 mmol) and chlorobenzene (175 ml) were added, and the mixture was stirred in a bath of 125° C. for 1 hour. Thereafter, the mixture was cooled and poured into ice--water, to which n-hexane was added. The insoluble matter was collected by filtration, and washed with chloroform. As a result, 15.0 of 6-hydroxy-8-methylcarbostyril was obtained as brown crystals (80.8%).

Workup

  1. temperatureThereafter, the mixture was cooled
  2. additionpoured into ice
  3. filtrationThe insoluble matter was collected by filtration
  4. washwashed with chloroform

Sources & evidence

ORD record
ord-5122579b25614e5eb5fe6c161b3885c0
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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