Toluene → HCID 178492346, compound

HRID 544404Notes

Reaction equation

HRID 544404 reaction equation
C1(C)C=CC=CC=1.C([Al](CC(C)C)CC(C)C)C(C)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1.[OH:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[CH:33][C:32]=1[C:41](OCC)=[O:42]>C(Cl)Cl>[OH:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[CH:33][C:32]=1[C:41]([NH:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=1)=[O:42]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7732P-AnisidineHCID 16682931TriisobutylaluminumHCID 178469510HCID 178469510, compound

Product 1

HCID 178492346HCID 178492346, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

230 ml of a toluene solution of triisobutyl aluminum were added with stirring at 8°-10° C. over 30 minutes to a mixture of 61.5 gof p-anisidine in one liter of anhydrous methylene chloride and then 21.7 gof ethyl 4-hydroxy-3-quinoline-carboxylate [described in J.A.C.S., Vol. 68 (1946), p. 1264] were added to the mixture in small portions. The mixture was refluxed for 20 hours and was evaporated to dryness. The residue was taken up in a mixture of 500 g of ice and 500 ml of aqueous 6 N hydrochloric acid and the mixture was stirred for 6 hours and vacuum filtered. The recovered product was washed with water until there were no chloride ions in the wash water, dried at 100° C. and was crystallized from acetic acid to obtain 23.54 g of 4-hydroxy-N-(4-methoxyphenyl)-3-quinoline-carboxamide melting at >260° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. customwas evaporated to dryness
  3. additionThe residue was taken up in a mixture of 500 g of ice and 500 ml of aqueous 6 N hydrochloric acid
  4. filtrationvacuum filtered
  5. washThe recovered product was washed with water until there
  6. customdried at 100° C.
  7. customwas crystallized from acetic acid

Sources & evidence

ORD record
ord-c8ad0e9869b34c8fbb3dbfb0a43e9f85
Source dataset
uspto-grants-1984_05
Patent number
US04450167

Reaction notes

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