Hydrochloric Acid → HCID 13787417, compound

HRID 1165216Notes

Reaction equation

HRID 1165216 reaction equation
[OH-].[K+].CC1C=CC(S([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][C:21]([C:23]2[C:24]3[CH:25]=[CH:26][NH:27][C:28]=3[CH:29]=[CH:30][CH:31]=2)=[O:22])(=O)=O)=CC=1.O.Cl>C(O)C>[OH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([C:23]1[C:24]2[CH:25]=[CH:26][NH:27][C:28]=2[CH:29]=[CH:30][CH:31]=1)=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 13787416HCID 13787416, compound

Product 1

HCID 13787417HCID 13787417, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

250 ml of a solution of potassium hydroxide in ethanol at 10 g per 100 ml were added to a suspension of 25 g of N-[2-[(4-methylphenyl)sulfonyloxy]phenyl]-1H-indol-4-carboxamide in 50 ml of ethanol at 95° C. with stirring under an inert atmosphere and the mixture was stirred for 21 hours. 1 liter of iced water was added, and the mixture was acidified with a concentrated aqueous solution of hydrochloric acid, followed by stirring for a further 15 minutes, filtering, drying and triturating at reflux in 1.5 liters of methylene chloride. After concentrating to about 300 ml, filtering and drying at 80° C. under reduced pressure, 13 g of N-(2-hydroxyphenyl)-1H-indol-4-carboxamide melting at ≃208° C. were obtained.

Workup

  1. stirringthe mixture was stirred for 21 hours
  2. stirringby stirring for a further 15 minutes
  3. filtrationfiltering
  4. customdrying
  5. customtriturating
  6. temperatureat reflux in 1.5 liters of methylene chloride
  7. concentrationAfter concentrating to about 300 ml
  8. filtrationfiltering
  9. dry with materialdrying at 80° C. under reduced pressure, 13 g of N-(2-hydroxyphenyl)-1H-indol-4-carboxamide melting at ≃208° C.
  10. customwere obtained

Sources & evidence

ORD record
ord-a6dda4c6691c4502b96ef5be53988d21
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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