Potassium Carbonate → 2-(3-Amino-5-methoxycarbonylphenylamino)-3-nitropyridine

HRID 2230980Notes

Reaction equation

HRID 2230980 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]=[C:20]([NH2:22])[CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[NH2:11][C:12]1[CH:21]=[C:20]([NH:22][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 7010431Methyl 3,5-diaminobenzoate

Product 1

HCID 227240642-(3-Amino-5-methoxycarbonylphenylamino)-3-nitropyridineYield 20.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (3.20 g), methyl 3,5-diaminobenzoate (3.20 g) and potassium carbonate (4.0 g) in 1,4-dioxane (60 ml) was stirred under reflux for 4 hours. After cooling, insoluble materials were removed by filtration and the filtrate was concentrated. The residue was chromatographed on silica gel column (5% methanol in chloroform) to give 2-(3-amino-5-methoxycarbonylphenylamino)-3-nitropyridine (1.12 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. custominsoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe residue was chromatographed on silica gel column (5% methanol in chloroform)

Sources & evidence

ORD record
ord-9d0e348567374bf7be4f5624695a05c1
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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