Water → HCID 15053101, compound

HRID 1654055Notes

Reaction equation

HRID 1654055 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.C([O-])([O-])=O.[K+].[K+].Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].O>CN(C=O)C>[N+:24]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:18]=1[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 160545-HydroxyindoleHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 15053101HCID 15053101, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-hydroxyindole (7.45 g) in 100 ml of DMF was added K2CO3 (10.4 g). This mixture was stirred for 10 minutes at room temperature and then a solution of 4-chloro-3-nitropyridine (11.89 g) in 50 ml DMF was added dropwise. The reaction was allowed to proceed for 24 hours at room temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and saturated NaCl solution and dried over MgSO4. After filtration, the solvent was evaporated to yield an oil (15.4 g). This material was eluted with 5% ethyl acetate/DCM on a silica gel column via HPLC. The desired fractions were concentrated to yield a solid, 1.35 g, m.p. 182°-184° C.

Workup

  1. waitto proceed for 24 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-80e7be3128d24214a47dff0f84b07ddb
Source dataset
uspto-grants-1995_04
Patent number
US05405856

Reaction notes

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