Picolyl chloride hydrochloride → HCID 66842332, compound

HRID 1158830Notes

Reaction equation

HRID 1158830 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[Cl-].[NH4+]>CN1CCCC1=O>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 25517Ammonium ChlorideHCID 785026-Nitro-1H-indole

Product 1

HCID 66842332HCID 66842332, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

—Sodium hydride (60% dispersion in oil, 15.5 g, 319 mmol) was added in portions to a solution of 6-nitroindole (23.5 g, 145 mmol) in 1-methyl-2-pyrrolidinone (1000 ml). After 45 min. stirring, 2-chloromethyl-pyridine hydrochloride (28.2 g, 174 mmol) was added in portions. Stirring was continued for 1 h and the reaction mixture was poured into a saturated aqueous solution of ammonium chloride. The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (heptane/ethyl acetate 1:1→ethyl acetate) afforded 6-nitro-1-pyridin-2-ylmethyl-1H-indole (30 g).

Workup

  1. stirringStirring
  2. waitwas continued for 1 h
  3. extractionThe product was extracted into ethyl acetate
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89c5af6e948a448eaee69ebcd064a16d
Source dataset
uspto-grants-2010_10
Patent number
US07812036B2

Reaction notes

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