Methyl iodide → Methyl 2-chloro-5-nitroisonicotinate

HRID 77391

반응식

HRID 77391 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[C:14](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1)[C:5]([O:7][CH3:14])=[O:6]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 184406222-Chloro-5-nitroisonicotinic acid2회

생성물 1

HCID 45480451Methyl 2-chloro-5-nitroisonicotinate수율 90.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-chloro-5-nitroisonicotinic acid (Intermediate 25A) (0.64 g, 3.17 mmol) in DMF (15 mL) under nitrogen was added sodium carbonate (1.0 g, 9.51 mmol). Reaction cooled in an ice bath and methyliodide (1.35 g, 9.51 mmol) was added dropwise. After complete addition, reaction allowed to warm to room temperature and stirred overnight under nitrogen. The reaction mixture was filtered and concentrated. The resultant crude material was purified by a 20 g silica column eluting with 40% ethylacetate in hexane to afford methyl 2-chloro-5-nitroisonicotinate (0.62 g, 2.86 mmol).

후처리

  1. customReaction
  2. temperaturecooled in an ice bath
  3. additionAfter complete addition, reaction
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated
  6. customThe resultant crude material was purified by a 20 g silica column
  7. washeluting with 40% ethylacetate in hexane

출처 및 근거

ORD 기록
ord-780c14261612436a84ead8ce4bed271c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841289B2

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