Ammonium formate → N-cyclopropylbenzene-1,2-diamine

HRID 878474Notes

Reaction equation

HRID 878474 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:11]([O-])=O)[CH2:3][CH2:2]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:1]1([NH:4][C:5]2[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10487549N-cyclopropyl-2-nitroaniline

Product 1

HCID 10582926N-cyclopropylbenzene-1,2-diamineYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-cyclopropyl-2-nitroaniline (365 mg, 2.05 mmol) and ammonium formate (516 mg, 8.2 mmol) in methanol was added catalytic amount of palladium on carbon (5%). The mixture was heated to reflux under a nitrogen atmosphere overnight and filtered. The filtrate was concentrated and purified by biotage column chromatography to give N1-cyclopropylbenzene-1,2-diamine (296 mg)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by biotage column chromatography

Sources & evidence

ORD record
ord-c0e1c4ba7de948509b9627b6bb3aa862
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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