Ethyl Acetate → HCID 22724184, compound

HRID 2230953Notes

Reaction equation

HRID 2230953 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[N:15]([CH3:19])[C:16](=[O:18])[CH3:17].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:19][N:15]([C:14]1[CH:13]=[C:12]([NH:11][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:22]=[CH:21][CH:20]=1)[C:16](=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 796132-Chloro-3-nitropyridineHCID 516892Sodium BicarbonateHCID 10607115N-(3-aminophenyl)-N-methylacetamide

Product 1

HCID 22724184HCID 22724184, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (1.96 g) and 3′-amino-N-methylacetanilide (2.03 g) in toluene (20 ml) was refluxed for 7 hours. The mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate solution. The organic phase was separated, washed with brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 2-[3-(N-methylacetamido)phenylamino]-3-nitropyridine (872 mg).

Workup

  1. temperaturewas refluxed for 7 hours
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-d1118bc2fc004893ac6d1f9294cd815d
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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