Nitric Acid → 2-Chloro-5-methoxy-3-methyl-4-nitropyridine 1-oxide

HRID 69315노트

반응식

HRID 69315 반응식
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH3:14])=[CH:8][N+:7]=1[O-:15].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[Cl:5][C:6]1[C:11]([CH3:12])=[C:10]([N+:1]([O-:4])=[O:2])[C:9]([O:13][CH3:14])=[CH:8][N+:7]=1[O-:15]

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 867178152-Chloro-5-methoxy-3-methylpyridine 1-oxide

생성물 1

HCID 867178162-Chloro-5-methoxy-3-methyl-4-nitropyridine 1-oxide

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
90 °C

실험 절차

Concentrated nitric acid (2.5 mL) was added drop-wise to a 0° C. solution of C2 (350 mg, 2.02 mmol) in concentrated sulfuric acid (2.5 mL). The reaction mixture was heated at 90° C. for 1 hour, then cooled to room temperature and poured onto crushed ice. The resulting mixture was neutralized to pH 6-7 with saturated aqueous sodium carbonate solution, and extracted with ethyl acetate. The combined organic layers were washed with water, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the product as a light yellow solid. Yield: 370 mg, 1.69 mmol, 84%. LCMS m/z 219.0, 221.1 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 8.65 (s, 1H), 3.94 (s, 3H), 2.31 (s, 3H).

후처리

  1. temperaturecooled to room temperature
  2. additionpoured
  3. customonto crushed ice
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-638a42ae056845ba92bf5d870e224a00
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822494B2

반응 노트

불러오는 중…