Water → HCID 19097363, compound

HRID 486059Notes

Reaction equation

HRID 486059 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 160545-HydroxyindoleHCID 203942-(Chloromethyl)quinoline

Product 1

HCID 19097363HCID 19097363, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-hydroxyindole (5.0 g), 2-chloromethylquinoline (7.0 g) and potassium carbonate (10.0 g) in N,N-dimethyl formamide (50 ml) was stirred at 80° C. for 4 hours. The cooled mixture was poured into water, and extracted with ethyl acetate. The combined organic layers were washed with water, dried over magnesium sulfate, and concentrated in vacuo. The crude product was recrystallized from ethanol to yield the title product (5.0 g), m.p. 134°-137° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-c9f2cfd0506749dd8ea2dd602b7d88c2
Source dataset
uspto-grants-1994_03
Patent number
US05290788

Reaction notes

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