N-Methylethylenediamine → HCID 69028482, compound

HRID 1866764Notes

Reaction equation

HRID 1866764 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=O.[CH3:15][NH:16][CH2:17][CH2:18][NH2:19]>>[CH3:15][N:16]1[CH2:17][CH2:18][N:19]=[C:5]1[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([CH3:1])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 8014N-MethylethylenediamineHCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Product 1

HCID 69028482HCID 69028482, compoundYield 75%

Conditions

Temperature
190 °C

Procedure

A solution of methyl 3-methyl-2-nitrobenzoate (3.0 g, 15.4 mmol) in N-methylethylene diamine (5 g, 68 mmol) was heated at reflux for 1.5 hour, at which point the solvent was removed at 130° C. under reduced pressure. The residue was then heated at 190° C. for 1.25 hour before being cooled on ice to give the title compound of Step A (75% pure) as a brown oil.

Workup

  1. temperatureat reflux for 1.5 hour, at which point the solvent
  2. customwas removed at 130° C. under reduced pressure
  3. temperaturebefore being cooled on ice

Sources & evidence

ORD record
ord-903047669bcf4964a042e1a9c81ad58f
Source dataset
uspto-grants-2009_12
Patent number
US07629463B2

Reaction notes

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