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

HRID 2204318ノート

反応式

HRID 2204318 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9cd98a3f32ea481aa19d3d89c6cd98da
出典データセット
uspto-grants-2016_06
特許番号
US09365576B2

反応ノート

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