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

HRID 655754노트

반응식

HRID 655754 반응식
[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]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 66707683ethyl 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylate2회

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a2e2600c47784d9d83e36584ef40b6d7
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071605B2

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