Water → HCID 18005131, compound

HRID 989185Notes

Reaction equation

HRID 989185 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 tide 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-41a0b3c2aca54a3d9fe4d37218d47017
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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