m-Aminoacetanilide → HCID 15296999, compound

HRID 2086760Notes

Reaction equation

HRID 2086760 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:19]=[CH:20][CH:21]=1)[NH:15][C:16](=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:16]([NH: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:21]=[CH:20][CH:19]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7604m-AminoacetanilideHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 15296999HCID 15296999, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (6.12 g), 3′-aminoacetanilide (5.80 g) and potassium carbonate (5.34 g) in toluene (50 ml) was refluxed for 5 hours. The mixture was cooled, and the solids were collected and washed with water, ethanol and isopropyl ether successively to give 2-(3-acetamidophenyl)amino-3-nitropyridine (5.88 g) as an orange solid.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureThe mixture was cooled
  3. customthe solids were collected
  4. washwashed with water, ethanol and isopropyl ether successively

Sources & evidence

ORD record
ord-d4186e54c9b14a40a9ef3d8b52014720
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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