Methylamine → HCID 86340167, compound

HRID 2275007Notes

Reaction equation

HRID 2275007 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16].[CH3:17][NH2:18]>CN(C)C=O>[CH3:16][O:15][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=1[NH:18][CH3:17])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 49757533Methyl 4-chloro-3-methoxy-5-nitrobenzoate

Product 1

HCID 86340167HCID 86340167, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 4-chloro-3-methoxy-5-nitrobenzoate (available from, for example, Apollo Scientific Ltd) (14 g, 57.0 mmol) was dissolved in N,N-dimethylformamide (DMF) (140 mL) and cooled to ˜0° C. in an ice/water bath. Methanamine (2M in THF) (114 mL, 228 mmol) was added dropwise with vigorous stirring using a dropping funnel and the mixture was flushed with nitrogen and heated at 80° C. for 3 hr. The mixture was allowed to cool to room temperature over the weekend. The reaction mixture was diluted with water (500 mL), and filtered under vacuum to give the title compound as an orange solid (13.69 g).

Workup

  1. customthe mixture was flushed with nitrogen
  2. temperatureheated at 80° C. for 3 hr
  3. temperatureto cool to room temperature over the weekend
  4. additionThe reaction mixture was diluted with water (500 mL)
  5. filtrationfiltered under vacuum

Sources & evidence

ORD record
ord-2a29b6b84f7446af8cf239e56ed68698
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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