HCID 19065937, compound → HCID 21280474, compound

HRID 414832Notes

Reaction equation

HRID 414832 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][N:14]=1>CS(C)=O.[OH-].[Na+]>[OH:25][CH:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:2][C:3]2[NH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[N:14][CH:15]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 19065937HCID 19065937, compoundHCID 178444966HCID 178444966, compound

Product 1

HCID 21280474HCID 21280474, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Chloromethyl indole (8 g, 0,048 mol) and 2-hydroxy-5-(1-hydroxyhexyl)pyridine (9.36 g, 0.048 mol) were dissolved in DMSO (250 ml) and to this mixture, 2N sodium hydroxide solution was added (25 ml, 0.05 mol). The clear, homogeneous reaction mixture became warm, and this mixture was stirred at room temperature overnight. The solution was poured into warer (500 ml), and was extracted thoroughly with ethyl acetate (4×50 ml). The combined extract was washed with 1N sodium hydroxide sclution, water and brine. After drying the organic extract over MgSO4, all volatiles were removed to leave a brown oil (9 g). This crude product was purified by HPLC (silica gel, 20% ethyl acetate in hexane) to yield the pure product (8.6 g, 55%) as a yellowish semi-solid.

Workup

  1. additionwas added (25 ml, 0.05 mol)
  2. temperatureThe clear, homogeneous reaction mixture became warm
  3. additionThe solution was poured into warer (500 ml)
  4. extractionwas extracted thoroughly with ethyl acetate (4×50 ml)
  5. extractionThe combined extract
  6. washwas washed with 1N sodium hydroxide sclution, water and brine
  7. customAfter drying the
  8. extractionorganic extract over MgSO4
  9. customall volatiles were removed

Sources & evidence

ORD record
ord-b95c481f7aba4ea28ab128d59cf00da2
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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