Tetrahydrofuran → HCID 20098356, compound

HRID 1165243Notes

Reaction equation

HRID 1165243 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.[CH:11]1[C:16]([Cl:17])=[CH:15][C:14]([C:18]([OH:20])=O)=[C:13](O)[CH:12]=1.C1(N=C=NC2CCCCC2)CCCCC1.[O:37]1CCCC1>>[Cl:17][C:16]1[CH:11]=[C:12]([OH:37])[CH:13]=[C:14]([CH:15]=1)[C:18]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)=[O:20]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 94475-Chlorosalicylic AcidHCID 10868Dicyclohexylcarbodiimide2×HCID 5834314-Aminoindole

Product 1

HCID 20098356HCID 20098356, compound

Procedure

A mixture of 3.96 g of 4-amino-1H-indole, 75 ml of tetrahydrofuran, 5.16 g of 5-chloro-salicyclic acid and 6.2 g of dicyclohexylcarbodiimide was refluxed for 2 hours and after the addition of another 0.62 g of dicyclohexylcarbodiimide, the mixture was refluxed for one hour, cooled and was filtered. The filtrate was evaporated to dryness under reduced pressure at 50° C. and the residue was taken up in ethyl acetate. The solution was washed with 2N hydrochloric acid, dried and evaporated to dryness under reduced pressure at 50° C. The residue was chromatographed over silica and was eluted with a 9-1 mixture of chloroform-ethyl acetate to obtain 3.9 g of 5-chloro-3-hydroxy-N-(1H-indol-4-yl)-benzamide melting at 248° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturethe mixture was refluxed for one hour
  3. temperaturecooled
  4. filtrationwas filtered
  5. customThe filtrate was evaporated to dryness under reduced pressure at 50° C.
  6. washThe solution was washed with 2N hydrochloric acid
  7. customdried
  8. customevaporated to dryness under reduced pressure at 50° C
  9. customThe residue was chromatographed over silica
  10. washwas eluted with a 9-1 mixture of chloroform-ethyl acetate

Sources & evidence

ORD record
ord-f0603a40952f4c9c9dc664b9267a897c
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

Loading…