Pyridine → HCID 22177449, compound

HRID 2308119Notes

Reaction equation

HRID 2308119 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[N+:14]([C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[C:20](Cl)=[O:21])([O-:16])=[O:15].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:20](=[O:21])[C:19]1[CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 74323,5-Dinitrobenzoyl chlorideHCID 7416311-Bromo-1-undecanol

Product 1

HCID 22177449HCID 22177449, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

11.4 g (45.4 mmol) 11-bromo-1-undecanol, 11.0 g (47.7 mmol) 3,5-dinitrobenzoyl chloride and 54 mg 4-dimethylaminopyridine were dissolved in 94 ml dichloromethane. The solution was subsequently cooled to 0° C. and then 18.3 ml is (227 mmol) pyridine was added dropwise, in the course of 25 minutes. After 4.5 hours at 0° C. the reaction mixture was partitioned between dichloromethane and water. The organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 200 g silica gel using toluene yielded 18.1 g (90%) 3,5-dinitrobenzoic acid 11-bromoundecyl ester as yellow powder.

Workup

  1. additionwas added dropwise, in the course of 25 minutes
  2. customAfter 4.5 hours at 0° C. the reaction mixture was partitioned between dichloromethane and water
  3. washThe organic phase was washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-7627ee13f0b643cf8e69a1906018ad5a
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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