Ammonium Chloride → 5-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-one

HRID 873800노트

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HRID 873800 반응식
[Cl:1][C:2]1[C:3](=[O:12])[N:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[NH4+].[Cl-]>[Fe].CCO>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3](=[O:12])[N:4]([CH3:11])[CH:5]=1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 867031063-chloro-1-methyl-5-nitropyridin-2(1H)-one

생성물 1

HCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-one수율 78%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

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온도
85 °C

실험 절차

To a stirred solution of 3-chloro-1-methyl-5-nitropyridin-2(1H)-one (Step 5.1) (10.38 g, 55.0 mmol), EtOH (200 mL) and NH4Cl (79 mL, 550 mmol) was added iron (9.22 g, 165 mmol). The reaction mixture was stirred for 1 hr at 85° C., filtered through a pad of celite, and concentrated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 2-10%) to afford the title product (6.77 g, 42.7 mmol, 78% yield) as a black solid. tR: 0.29 min (LC-MS 1); ESI-MS: 159 [M+H]+ (LC-MS 1); Rf=0.28 (CH2Cl2/MeOH 9:1).

후처리

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated
  3. customThe crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 2-10%)

출처 및 근거

ORD 기록
ord-285d7c991a7541febff07280f478416e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975417B2

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