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

HRID 2204318노트

반응식

HRID 2204318 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9cd98a3f32ea481aa19d3d89c6cd98da
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365576B2

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