Pyridine → HCID 86590765, compound

HRID 1008090Notes

Reaction equation

HRID 1008090 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([NH:17][CH2:18][CH2:19][OH:20])[C:11]([CH3:21])=[C:10]([CH3:22])[N:9]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([NH:17][CH2:18][CH2:19][O:20][C:23](=[O:25])[CH3:24])[C:11]([CH3:21])=[C:10]([CH3:22])[N:9]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21913142HCID 21913142, compound

Product 1

HCID 86590765HCID 86590765, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Pyridine (1.0 mL, 12 mmol) and 4-dimethylaminopyridine (DMAP) (0.005 g, 0.04 mmol) was added to a solution of 2-(2-chloro-5,6-dimethyl-3-nitropyridin-4-ylamino)ethanol (0.50 g, 2.0 mmol) in anhydrous dichloromethane (4.5 mL). Under a nitrogen atmosphere, acetic anhydride (0.8 mL, 8 mmol) was added, and the yellow solution was stirred at room temperature for 1.3 hours. The volatiles were removed under reduced pressure, and the residual yellow oil was dissolved in dichloromethane. The solution was washed with aqueous sodium bicarbonate, water, and brine, and then dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 0.55 g of acetic acid 2-(2-chloro-5,6-dimethyl-3-nitropyridin-4-ylamino)ethyl ester as a yellow solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residual yellow oil was dissolved in dichloromethane
  3. washThe solution was washed with aqueous sodium bicarbonate, water, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d04d848352546189bf07d9e3c656b2a
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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