Ethyl Acetate → N-(4-Methyl-pyridin-3-yl)-benzene-1,2-diamine

HRID 80227Notes

Reaction equation

HRID 80227 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O.C(OCC)(=O)C>CO.CCCCCC.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 12361028(4-Methyl-pyridin-3-yl)-(2-nitro-phenyl)-amine

Product 1

HCID 12361029N-(4-Methyl-pyridin-3-yl)-benzene-1,2-diamineYield 100.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

10% Pd/C (100 mg) was charged portion wise to a solution of (4-methyl-pyridin-3-yl)-(2-nitro-phenyl)-amine (I-171a: 600 mg, 2.62 mmol) in methanol (15 mL) under nitrogen atmosphere. The resulting mixture was stirred at room temperature under hydrogen atmosphere for 2 hours. The reaction was monitored by TLC (80% ethyl acetate in hexane). The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to afford 525 mg of the product (98.91% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4bf8c7281929497089c44dd6fc354e6a
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

Loading…