Ethyl Acetate → HCID 22724184, compound

HRID 2086776Notes

Reaction equation

HRID 2086776 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-fa440064f40f4b7d8672060f1723b1a2
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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