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

HRID 2273591Notes

Reaction equation

HRID 2273591 reaction equation
C([O-])=O.[NH4+].[CH:5]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)([CH3:7])[CH3:6]>CO.[Pd]>[CH:5]([NH:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1)([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10583518N-Isopropyl-2-nitroaniline

Product 1

HCID 105587871-N-(propan-2-yl)benzene-1,2-diamineYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (960 mg, 15.0 mmol) is added to a solution of N-isopropyl-2-nitroaniline (550 mg, 3.03 mmol) in methanol. This may be followed by a catalytic amount of palladium on carbon (5%). The mixture may be refluxed overnight, cooled to room temperature and filtered. The filtrate may be concentrated by any applicable and the residue may be purified, for example by Biotage column chromatography to give N1-isopropylbenzene-1,2-diamine (398 mg)

Workup

  1. temperatureThe mixture may be refluxed overnight
  2. filtrationfiltered
  3. concentrationThe filtrate may be concentrated by any applicable and the residue

Sources & evidence

ORD record
ord-d1edce94facc449eaa30f802c7251202
Source dataset
uspto-grants-2015_09
Patent number
US09125901B2

Reaction notes

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