Salicylic Acid → 2-hydroxy-N-(1-methyl-1H-indol-4-yl)benzamide

HRID 1165230Notes

Reaction equation

HRID 1165230 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3]1.[C:12](O)(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[OH:15][C:14]1[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=1[C:12]([NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]2[CH3:1])=[O:20]

Participants

5

Reactant 3

HCID 338Salicylic Acid2×HCID 10868Dicyclohexylcarbodiimide2×HCID 221703071-methyl-1H-indol-4-amine

Product 1

HCID 200983612-hydroxy-N-(1-methyl-1H-indol-4-yl)benzamideYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5 g of 1-methyl-1H-indol-4-amine [prepared according to Ley (J. Chem. Soc. Chem. Com. (1982) p. 1356], 4.7 g of salicylic acid and 7 g of dicyclohexylcarbodiimide in 80 ml of tetrahydrofuran was refluxed for 24 hours and 20% of salicylic acid and of dicyclohexylcarbodiimide were added after 5 hours of refluxing. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by chromatography over silica (eluant: methylene chloride) to obtain 5.5 g of 2-hydroxy-N-(1-methyl-1H-indol-4-yl)benzamide melting at 211° C.

Workup

  1. temperatureof refluxing
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by chromatography over silica (eluant: methylene chloride)

Sources & evidence

ORD record
ord-f7410341b1504891a3eca1c3c9acde82
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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