Ethylenediamine → HCID 17960600, compound

HRID 1866758Notes

Reaction equation

HRID 1866758 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.[CH2:15]([NH2:18])[CH2:16][NH2:17]>>[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([C:5]2[NH:17][CH2:16][CH2:15][N:18]=2)[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Product 1

HCID 17960600HCID 17960600, compound

Conditions

Temperature
190 °C

Procedure

A solution of methyl 3-methyl-2-nitrobenzoate 3.13 g (16.1 mmol) in ethylenediamine (15 mL) was heated at reflux for 1.5 hours, at which point the solvent was removed at 130° C. under reduced pressure. The residue was then heated at 190° C. for 1.25 hours before being cooled on ice and purified by flash column chromatography (silica gel, 1% to 10% methanol in dichloromethane) to give the title compound of Step A (0.35 g) as a brown oil.

Workup

  1. temperatureat reflux for 1.5 hours, at which point the solvent
  2. customwas removed at 130° C. under reduced pressure
  3. temperaturebefore being cooled on ice
  4. custompurified by flash column chromatography (silica gel, 1% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0db13af461434945a9af780189f21129
Source dataset
uspto-grants-2009_12
Patent number
US07629463B2

Reaction notes

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