Water → HCID 21913198, compound

HRID 1245950Notes

Reaction equation

HRID 1245950 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1.[N:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:28][CH2:29][CH2:30][NH2:31])=[CH:23][CH:22]=1.O>CN(C=O)C>[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:31][CH2:30][CH2:29][O:28][CH2:27][C:24]2[CH:23]=[CH:22][N:21]=[CH:26][CH:25]=2)[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridineHCID 21913051HCID 21913051, compound

Product 1

HCID 21913198HCID 21913198, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (7.4 mL, 53 mmol) was added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (9.78 g, 44.2 mmol) in anhydrous DMF (200 mL). 2-(Pyridin-4-ylmethoxy)ethylamine (6.8 g, 45 mmol) was added, and the reaction was stirred at room temperature for 17.5 hours. The reaction solution was slowly added to water (1.8 L) and stirred for two hours to form a precipitate, which was isolated by filtration and washed with cold hexane (200 mL). The solid was dried under reduced pressure for one hour to provide 10.15 g of (2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)-[2-(pyridin-4-ylmethoxy)ethyl]amine as a yellow solid. An analysis by HPLC indicated that starting material and an isomer were present as impurities.

Workup

  1. stirringstirred for two hours
  2. customto form a precipitate
  3. customwhich was isolated by filtration
  4. washwashed with cold hexane (200 mL)
  5. customThe solid was dried under reduced pressure for one hour

Sources & evidence

ORD record
ord-4d0486ab08644a0ea2e6f58e1534d1e9
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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