Sodium Hydroxide → 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylic acid

HRID 655754ノート

反応式

HRID 655754 の反応式
[Cl:1][C:2]1[C:3]([C:13]#[N:14])=[C:4]([C:8]([O:10]CC)=[O:9])[NH:5][C:6]=1[CH3:7].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[C:3]([C:13]#[N:14])=[C:4]([C:8]([OH:10])=[O:9])[NH:5][C:6]=1[CH3:7]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 66707683ethyl 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylate2 回

生成物 1

HCID 594025744-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylic acid収率 90.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 670 mg (3.2 mmol) of ethyl 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylate (Intermediate 15) and 3.2 ml (3.2 mmol) 1N NaOH in 20 ml MeOH was heated at 100° C. in a microwave reactor for 2 h. The mixture was diluted with water and extracted with EtOAc. The EtOAc was washed with 1N NaOH. The combined aqueous layers were acidified with concentrated HCl and extracted 2 times with EtOAc, each extract being washed with brine. The combined EtOAc layers were dried over anhydrous MgSO4, filtered and the solvent was removed to give 535 mg of product as a solid. MS (ES) (M−H−): 183 for C7H5ClN2O2; NMR (d6-DMSO): 2.2 (s, 3H), 12.9 (s, 1H), 13.3 (s, 1H).

後処理

  1. extractionextracted with EtOAc
  2. washThe EtOAc was washed with 1N NaOH
  3. extractionextracted 2 times with EtOAc
  4. washeach extract being washed with brine
  5. dry with materialThe combined EtOAc layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed

出典と根拠

ORDレコード
ord-a2e2600c47784d9d83e36584ef40b6d7
出典データセット
uspto-grants-2011_12
特許番号
US08071605B2

反応ノート

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