Hydrochloric Acid → HCID 13787428, compound

HRID 1091136Notes

Reaction equation

HRID 1091136 reaction equation
C([Al](CC(C)C)CC(C)C)C(C)C.[NH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2.[C:24](OC)(=[O:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)[OH:27].Cl>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.C(Cl)Cl>[OH:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[C:24]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2)=[O:32]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4133Methyl SalicylateHCID 5834314-AminoindoleHCID 16682931Triisobutylaluminum

Product 1

HCID 13787428HCID 13787428, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

92 ml of a solution of 1.1 mol/l of triisobutylaluminum in toluene were added slowly with stirring under an inert atmosphere to a solution of 6.6 g of 4-aminoindole in 250 ml of chloroform. 9.6 ml of methyl salicylate were then added and the mixture was refluxed for 20 hours and then cooled to room temperature. 300 ml of N hydrochloric acid and 300 ml of methylene chloride were added and the organic phase was washed with water, dried, and evaporated to dryness under reduced pressure at 50° C. The residue was made into a paste with ether, filtered and dried at 60° C. under reduced pressure to obtain 9.4 g of 2-hydroxy-N-(1H-indol-4-yl)benzamide melting at ≃232° C.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure at 50° C
  5. filtrationfiltered
  6. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-15636254b0e34125a2dfe03ef45133b2
Source dataset
uspto-grants-1992_01
Patent number
US05084455

Reaction notes

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