Ammonium formate → 1-N-(2-methoxyethyl)benzene-1,2-diamine

HRID 2273596Notes

Reaction equation

HRID 2273596 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][CH2:7][CH2:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O>[Pd].CO>[CH3:5][O:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10375425N-(2-Methoxyethyl)-2-nitroaniline

Product 1

HCID 102614521-N-(2-methoxyethyl)benzene-1,2-diamineYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (727 mg, 11.3 mmol) followed by a catalytic amount of palladium on carbon (5%) is added to a solution of N-(2-methoxyethyl)-2-nitroaniline (426 mg, 2.17 mmol) in methanol. The mixture may be refluxed for an appropriate time period (such as overnight), cooled to an appropriate temperature (such as room temperature) and filtered. The filtrate may be concentrated and the residue may purified by Biotage column chromatography to give N1-(2-methoxyethyl)benzene-1,2-diamine (319 mg)

Workup

  1. temperatureThe mixture may be refluxed for an appropriate time period (such as overnight)
  2. filtrationfiltered
  3. concentrationThe filtrate may be concentrated
  4. customthe residue may purified by Biotage column chromatography

Sources & evidence

ORD record
ord-937e34ca3b234f7fba1c9fe743faf356
Source dataset
uspto-grants-2015_09
Patent number
US09125901B2

Reaction notes

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