Salicylaldehyde → HCID 22722275, compound

HRID 1581717Notes

Reaction equation

HRID 1581717 reaction equation
[N+:1]([C:4]1[CH:15]=[C:14]2[C:7]([NH:8][CH:9]=[C:10]2[CH2:11][CH2:12][NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:16](=O)[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].[OH-].[K+].[BH4-].[Na+]>C(O)C>[N+:1]([C:4]1[CH:15]=[C:14]2[C:7](=[CH:6][CH:5]=1)[NH:8][CH:9]=[C:10]2[CH2:11][CH2:12][NH:13][CH2:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[OH:19])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 14797Potassium HydroxideHCID 1512951H-Indole-3-ethanamine, 5-nitro-HCID 4311764Sodium borohydride

Product 1

HCID 22722275HCID 22722275, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Nitrotryptamine (6 mmol) and salicylaldehyde (7 mmol) are dissolved in ethanol (35 mL) buffered with potassium hydroxide (0.15 g) and treated with sodium borohydride (18 mmol) 8 h at 24° C. The ethanol is removed in vacuo and the residue partitioned between ether and water, the ether phase dried, evaporated and the oil chromatographed on silica gel with ethyl acetate-hexane to afford 2-{[2-(5-nitro-1H-indol-3-yl)-ethylamino]-methyl}-phenol. After hydrogenation over Pd/C as above, the residue is dissolved in pyridine (12 mL) and treated with methyl chloroformate (9 mmol). A brownish precipitate forms immediately upon addition of the chloroformate, which dissolves during 20 min. After a short time silica gel TLC (5% methanol-chloroform eluent) is performed to judge completion of the reaction. The mixture is evaporated to dryness and maintained at a vacuum of <0.1 mmHg at least 2 h. It is then dissolved in a small amount of methanol, and purified by reverse-phase HPLC with a gradient of water to methanol.

Workup

  1. customThe ethanol is removed in vacuo
  2. customthe residue partitioned between ether and water
  3. dry with materialthe ether phase dried
  4. customevaporated
  5. customthe oil chromatographed on silica gel with ethyl acetate-hexane

Sources & evidence

ORD record
ord-b2bbcd653cdc427bb77adfb41aa279fa
Source dataset
uspto-grants-2004_05
Patent number
US06730707B2

Reaction notes

Loading…