Water → HCID 14368439, compound

HRID 1762203Notes

Reaction equation

HRID 1762203 reaction equation
Cl[CH2:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][O:6][C:7]1[C:8]([N+:13]([O-:15])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[K].O>CN(C)C=O>[N+:13]([C:8]1[C:7]([O:6][CH2:5][C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=2[CH2:2][N:24]2[C:23](=[O:25])[C:22]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]3[C:20]2=[O:30])=[CH:12][CH:11]=[CH:10][N:9]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14368440HCID 14368440, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 14368439HCID 14368439, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-chloromethylbenzyloxy)-2-nitropyridine (4.09 g) and potassium phthalimide (2.99 g) in N,N-dimethylformamide (41 ml) was stirred at 50° C. for 9.5 hours. The reaction mixture was poured into water (200 ml) and extracted twice with ethyl acetate (250 ml). The combined extract was washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the resultant residue was recrystallized from ethyl acetate to give 2-nitro-3-(2-phthalimidomethylbenzyloxy)pyridine (2.7 g).

Workup

  1. extractionextracted twice with ethyl acetate (250 ml)
  2. extractionThe combined extract
  3. washwas washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resultant residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a3dd39394dc54268ae31b5faa3156479
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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