Water → HCID 18005131, compound

HRID 1603773Notes

Reaction equation

HRID 1603773 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].Cl.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22]Cl)[CH:17]=1.O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:22][C:18]1[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 225235-NitroindoleHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydride

Product 1

HCID 18005131HCID 18005131, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Nitroindole (0.49, 3 mmol) was treated with sodium hydride (0.198 g, 6.6 mmol) in dry dimethylformamide (20 ml). After 15 min at room temperature, 3-picolyl chloride hydrochloride (0.49 g, 3 mmol) was added and the mixture was stirred at room temperature for 24 h, then poured into water. The precipitate was filtered off, washed with water and dried to give the title compound (0.67 g, 88%), m.p. 131-4° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-e0b3dd5d352c4dda9e7fa1e17cea02b8
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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