Dimethylformamide → Methyl 5-chloro-2-methyl-3-nitrobenzoate

HRID 1501696

반응식

HRID 1501696 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:15]N(C=O)C.IC.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 230097625-Chloro-2-methyl-3-nitrobenzoic acid

생성물 1

HCID 53399191Methyl 5-chloro-2-methyl-3-nitrobenzoate수율 90%

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 5-chloro-2-methyl-3-nitrobenzoic acid (1 equiv.) in DMF (3 ml per 1 mmol), iodomethane (4 equiv.) and sodium carbonate (4 equiv.) were added. The resulting reaction mixture was stirred at 60° C. for 8 h. On completion, the reaction mixture was filtered and the inorganic solid residue washed with ethyl acetate. The combined filtrate was concentrated under vacuum till dryness. The residue was re-dissolved in ethyl acetate and washed with 5% sodium bicarbonate solution followed by 5M HCl solution. Organic layer was finally washed with brine, dried over sodium sulfate and concentrated to afford pure methyl 5-chloro-2-methyl-3-nitrobenzoate (90-95%).

후처리

  1. customThe resulting reaction mixture
  2. filtrationOn completion, the reaction mixture was filtered
  3. washthe inorganic solid residue washed with ethyl acetate
  4. concentrationThe combined filtrate was concentrated under vacuum till dryness
  5. dissolutionThe residue was re-dissolved in ethyl acetate
  6. washwashed with 5% sodium bicarbonate solution
  7. washOrganic layer was finally washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ac012fbd129241c5baccfa8f1a71d5b9
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206157B2

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