Hydrochloric Acid → HCID 20098393, compound

HRID 1768977Notes

Reaction equation

HRID 1768977 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(OC)(=O)[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>[NH:19]1[C:20]2[C:16](=[C:15]([NH:14][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[OH:27])[CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:18]1

Participants

8

Reactant 4

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

Product 1

HCID 20098393HCID 20098393, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

92 ml of a 1.1 mole/liter solution of triisobutylaluminum in toluene were added with stirring under an inert atmosphere to a solution of 6.6 g of 4-amino indole in 250 ml of chloroform and then 9.6 ml of methyl salicylate were added. The mixture was refluxed for 20 hours and then cooled to ambient temperature. 300 ml of N hydrochloric acid and 300 ml of methylene chloride were added, followed by washing with water, drying over a desiccant, filtering, evaporating to dryness under reduced pressure at 50° C., triturating with ether, filtering and drying at 60° C. under reduced pressure to obtain 9.4 g of 2-[N-(1H-indol-4-yl)amino]phenol melting at ≃232° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. washby washing with water
  3. customdrying over a desiccant,
  4. filtrationfiltering
  5. customevaporating to dryness under reduced pressure at 50° C.
  6. customtriturating with ether
  7. filtrationfiltering
  8. customdrying at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-1c6320cd32ad4572911f225c7bdd9f11
Source dataset
uspto-grants-1995_01
Patent number
US05380722

Reaction notes

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