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

HRID 1748333Notes

Reaction equation

HRID 1748333 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-diamine

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 20% palladium on carbon (50 mg, Degussa type) followed by ammonium formate (1.4 g, 23 mmol) and the reaction is stirred overnight. The suspension is carefully filtered through a bed of Celite and the filtrate is rinsed with additional ethanol (10 mL). The filtrate is concentrated and the residue is partitioned between water and ethyl acetate. The organic layer is dried (Na2SO4) and concentrated.

Workup

  1. filtrationThe suspension is carefully filtered through a bed of Celite
  2. washthe filtrate is rinsed with additional ethanol (10 mL)
  3. concentrationThe filtrate is concentrated
  4. customthe residue is partitioned between water and ethyl acetate
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-44c022916ffa40a4a4f2816478ed02d7
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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