Ammonium Chloride → 5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one

HRID 2204318Notes

Reaction equation

HRID 2204318 reaction equation
[NH4+].[Cl-].[Cl:3][C:4]1[C:5](=[O:22])[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1>CCO.[Fe]>[NH2:10][C:8]1[CH:9]=[C:4]([Cl:3])[C:5](=[O:22])[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 867031253-chloro-1-(4-methoxy-benzyl)-5-nitro-1H-pyridin-2-one

Product 1

HCID 867031245-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A saturated aqueous solution of NH4Cl (99 mL) was added to a solution of 3-chloro-1-(4-methoxy-benzyl)-5-nitro-1H-pyridin-2-one (Step O5) (6.8 g, 23.0 mmol) in EtOH (300 mL). After stirring for 15 min, iron powder (6.4 g, 115 mmol) was added and the resulting mixture was heated to reflux, stirred for 1 h, cooled to rt and concentrated. The residue was diluted with EtOH and the mixture was filtered through a pad of celite. The filtrate was concentrated. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 100:0→96.5:3.5). ESI-MS: tR=0.61 min, [M+H]+ 265/267 (LC-MS 1); Rf=0.53 (9:1 CH2Cl2/MeOH).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. stirringstirred for 1 h
  4. concentrationconcentrated
  5. additionThe residue was diluted with EtOH
  6. filtrationthe mixture was filtered through a pad of celite
  7. concentrationThe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 100:0→96.5:3.5)

Sources & evidence

ORD record
ord-9cd98a3f32ea481aa19d3d89c6cd98da
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

Loading…