Water → HCID 70574675, compound

HRID 1680487Notes

Reaction equation

HRID 1680487 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]2[NH:18][CH:19]=[CH:20][N:21]=2)=[CH:8]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:3][CH2:4][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]2[NH:21][CH:20]=[CH:19][N:18]=2)=[CH:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 70574941HCID 70574941, compound

Product 1

HCID 70574675HCID 70574675, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-ethoxycarbonylmethyl-3-(1-imidazolylmethyl)indole (1.42 g) in dry tetrahydrofuran (30 ml) was added portionwise to a stirred suspension of lithium aluminium hydride (0.19 g) in dry nitrogen. The mixture was heated under reflux with stirring for 6 hours, and then cooled and a further 0.19 g of lithium aluminium hydride was added. The mixture was heated under reflux with stirring for a further period of 3 hours and then cooled. Water (0.4 ml) was added cautiously with stirring and cooling followed by 5 N sodium hydroxide solution (0.4 ml) and a further 1.2 ml of water. The mixture was filtered and the filtrate was evaporated. The residue was chromatographed on silica gel, eluting with a mixture of chloroform and methanol (20:1) to give a solid. Crystallisation from ethyl acetate/petrol (b.p. 60°-80° C.) gave 1-(2-hydroxyethyl)-3-(1-imidazolylmethyl)indole, (0.55 g), m.p. 134°-135° C. Found: C, 69.75; H, 6.25; N, 17.46. C14H15N3O requires: C, 69.69; H, 6.27; N, 17.42%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. temperatureThe mixture was heated
  5. temperatureunder reflux
  6. stirringwith stirring for a further period of 3 hours
  7. temperaturecooled
  8. stirringwith stirring
  9. temperaturecooling
  10. filtrationThe mixture was filtered
  11. customthe filtrate was evaporated
  12. customThe residue was chromatographed on silica gel
  13. washeluting with a mixture of chloroform and methanol (20:1)
  14. customto give a solid
  15. customCrystallisation from ethyl acetate/petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-69d911f0215f4153aeb72d4a1bac3db1
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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