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

HRID 1521728Notes

Reaction equation

HRID 1521728 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[NH:6][CH:7]([CH3:9])[CH3:8])([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:9][CH:7]([NH:6][C:5]1[C:4]([NH2:1])=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8]

Participants

5

Reactant 2

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

Product 1

HCID 105587871-N-(propan-2-yl)benzene-1,2-diamineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-nitro-N-(propan-2-yl)aniline (828 mg, 4.6 mmol) in ethanol (10 mL) under a nitrogen atmosphere is carefully added 20% palladium on carbon (50 mg, Degussa type) followed by ammonium formate (1.4 g, 23 mmol) and the reaction is stirred for 16 h. The suspension is carefully filtered through a bed of Celite and the filter cake is rinsed with additional ethanol (10 mL). The filtrate is concentrated and the residue is partitioned between H2O and ethyl acetate. The organic layer is dried (Na2SO4) and concentrated and the residue is purified by chromatography through a short bed of silica gel using 5% methanol/CH2Cl2 affords the title compound (552 mg, 80%) as an oil.

Workup

  1. filtrationThe suspension is carefully filtered through a bed of Celite
  2. washthe filter cake is rinsed with additional ethanol (10 mL)
  3. concentrationThe filtrate is concentrated
  4. customthe residue is partitioned between H2O and ethyl acetate
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue is purified by chromatography through a short bed of silica gel using 5% methanol/CH2Cl2

Sources & evidence

ORD record
ord-b0a9c5ed10184b5ba39c7cb47364b683
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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