Ammonium formate → HCID 21914174, compound

HRID 730929Notes

Reaction equation

HRID 730929 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[CH:6]=[CH:7][CH:8]=1)#[N:2].C([O-])=O.[NH4+]>CO.O1CCCC1.[Zn]>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[NH2:15])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 21914164HCID 21914164, compound

Product 1

HCID 21914174HCID 21914174, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Zinc dust (20.26 g, 310 mmol) was added in portions over five minutes to a solution of 2-(3-cyanophenyl)-4-nitroanisole (15.7 g, 62 mmol) and ammonium formate (19.48 g, 310 mmol) in methanol (500 mL) and tetrahydrofuran (500 mL). The reaction was complete after stirring for one hour at room temperature. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified using flash chromatography on silica gel eluting with 5% methanol in dichloromethane to give 3-(3-cyanophenyl)-4-methoxyaniline (10 g, 44 mmol) as a yellow oil.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified

Sources & evidence

ORD record
ord-22cd6381629c448dbab72b069460b4c0
Source dataset
uspto-grants-2009_09
Patent number
US07582765B2

Reaction notes

Loading…