Sodium Carbonate → N-(2-methoxy-4-nitrophenyl)-N-(2-pyrid-2-ylethyl)amine

HRID 33090

Reaction equation

HRID 33090 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].C(=O)([O-])[O-].[Na+].[Na+].CCN[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C[N:29]1C(=O)C[CH2:31][CH2:30]1>O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH:29][CH2:30][CH2:31][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 705192-Chloro-5-nitroanisoleHCID 118047452-(Ethylamino)pyridine

Product 1

HCID 23104829N-(2-methoxy-4-nitrophenyl)-N-(2-pyrid-2-ylethyl)amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

5.62 g (0.03 mol) of 2-chloro-5-nitroanisole, 4 g (0.038 mol) of sodium carbonate, 4.5 g (0.037 mol) of 2-(2-ethylamino)pyridine, and 25 ml of NMP were introduced into a three-necked flask under nitrogen. The mixture was heated to 10° C. After reaction for 6 days, the reaction mixture was cooled and 75 ml of distilled water were then added slowly with vigorous stirring. The nitro derivative appeared in the form of a brown semi-solid, and was extracted with dichloromethane and then purified on a column of silica, eluting with 2/3 ethyl acetate/heptane. 2.1 g of expected nitro derivative (9) were obtained in the form of an orange solid. The proton NMR and 13C spectra and microanalyses were in accordance with the expected structure of the product.

Workup

  1. customAfter reaction for 6 days
  2. temperaturethe reaction mixture was cooled
  3. extractionwas extracted with dichloromethane
  4. custompurified on a column of silica
  5. washeluting with 2/3 ethyl acetate/heptane

Sources & evidence

ORD record
ord-4b2ff165892d44d880115ac6d39696f1
Source dataset
uspto-grants-2008_09
Patent number
US07429278B2

Linked notes

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