m-Toluidine → HCID 70665295, compound

HRID 333547Notes

Reaction equation

HRID 333547 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1>C(O)CCC>[CH3:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH:19][C:20]2[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 8471TriethylamineHCID 8183002-Chloro-5-methyl-3-nitropyridine

Product 1

HCID 70665295HCID 70665295, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-chloro-5-methyl-3-nitropyridine (13 g, 75 mmol), triethylamine (12.6 mL, 90 mmol), and m-toluidine (9.8 mL, 90 mmol) in 200 mL butanol was heated overnight under nitrogen. The solvent was evaporated, and the residue dissolved in dichloromethane. The organic layer was washed twice with water, brine, dried over magnesium sulfate, filtered, and evaporated (15.5 g, 85%).

Workup

  1. temperaturewas heated overnight under nitrogen
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washThe organic layer was washed twice with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated (15.5 g, 85%)

Sources & evidence

ORD record
ord-f030df7903364391bb8dcbea1698fb42
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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