Methylamine → HCID 58522649, compound

HRID 81343Notes

Reaction equation

HRID 81343 reaction equation
C([O:3][C:4](=O)[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=1[C:14](=O)[CH3:15])C.[CH3:18][NH2:19]>CO.[O-]S([O-])(=O)=O.[Mg+2].ClCCl>[CH3:18][N:19]1[C:14](=[CH2:15])[C:6]2[C:5](=[C:10]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:8][CH:7]=2)[C:4]1=[O:3]

Participants

6

Reactant 2

HCID 6329MethylamineHCID 53434730Ethyl 2-acetyl-6-nitrobenzoate

Product 1

HCID 58522649HCID 58522649, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 24083Sulfuric acid magnesium salt (1:1)Solvent

Procedure

Ethyl-2-acetyl-6-nitrobenzoate (11.12 g) is suspended in a mixture of MeOH (70 mL) and MgSO4. Methylamine (2 molar in THF, 28.13 mL) is added dropwise and the solution is stirred for 15 min at this temperature. Then it is preheated to 70° C. for 18 h. The solvent is eliminated in vacuo, the residue is taken up in dichloromethane (100 mL), washed with sodium chloride solution (10%) dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo. For purification it is recrystallised from toluene (250 mL).

Workup

  1. waitThen it is preheated to 70° C. for 18 h
  2. washwashed with sodium chloride solution (10%)
  3. customdried on magnesium sulphate
  4. filtrationfiltered off from the desiccant and the solvent
  5. customFor purification it
  6. customis recrystallised from toluene (250 mL)

Sources & evidence

ORD record
ord-bf2e1c2a43e14672afa57ac8c6f817de
Source dataset
uspto-grants-2014_09
Patent number
US08846689B2

Reaction notes

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