Dicyclohexylcarbodiimide → HCID 20098401, compound

HRID 1769000Notes

Reaction equation

HRID 1769000 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH:11][C:12]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:13]=1[C:14](O)=[O:15].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:22][O:21][C:19]1[CH:18]=[CH:17][C:13]([C:14]([NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[CH:5][NH:6]3)=[O:15])=[C:12]([OH:11])[CH:20]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 752314-Methoxysalicylic AcidHCID 5834314-Aminoindole

Product 1

HCID 20098401HCID 20098401, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.96 g of 4-amino-1H-indol, 70 ml of tetrahydrofuran. 5 g of 2-hydroxy-4-methoxy-benzoic acid and 6.2 g of dicyclohexylcarbodiimide was refluxed for 24 hours and was evaporated to dryness under reduced pressure at 50° C. The residue was taken up in ethyl acetate and excess 4-amino-1H-indole was removed by washing with 2N hydrochloric acid. The mixture was evaporated to dryness under reduced pressure and the residue was taken up in ether and dried at 50° C. to obtain 7.1 g of 4-methoxy-2-hydroxy-N-(1H-indol-4-yl)-benzamide melting at 190° C.

Workup

  1. customwas evaporated to dryness under reduced pressure at 50° C
  2. customexcess 4-amino-1H-indole was removed
  3. washby washing with 2N hydrochloric acid
  4. customThe mixture was evaporated to dryness under reduced pressure
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-fddf8d693ce74f4d9bec1f95e83c4dc2
Source dataset
uspto-grants-1995_01
Patent number
US05380722

Reaction notes

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