Methyl iodide → Methyl 2-chloro-5-nitroisonicotinate

HRID 77391

反応式

HRID 77391 の反応式
[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]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 184406222-Chloro-5-nitroisonicotinic acid2 回

生成物 1

HCID 45480451Methyl 2-chloro-5-nitroisonicotinate収率 90.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-780c14261612436a84ead8ce4bed271c
出典データセット
uspto-grants-2014_09
特許番号
US08841289B2

関連ノート

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