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Dimethylformamide → Methyl 5-methoxy-2-nitrobenzoate

HRID 1672322
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HRID 1672322 반응식
O[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)C(O)=O.[C:14](=[O:17])([O-])[O-:15].[K+].[K+].[CH3:20]I.CN([CH:25]=[O:26])C>O>[CH3:20][O:15][C:14](=[O:17])[C:4]1[CH:3]=[C:2]([O:26][CH3:25])[CH:10]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118825-Hydroxy-2-nitrobenzoic acid

생성물 1

HCID 12719167Methyl 5-methoxy-2-nitrobenzoate

시약·촉매·용매 1

HCID 962Water용매

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온도
75 °C

실험 절차

20 g (0.109 mol) of 5-hydroxy-2-nitro-benzoic acid (Example 44a) and 32.7 g (0.247 mol) potassium carbonate are stirred for 15 min in 163 ml of DMF. 23.8 ml (0.383 mol) of methyl iodide are added and the reaction mixture is stirred for 4 h at 75° C. The cold reaction mixture is diluted with water and is extracted with ether. After drying the organic phase with sodium sulfate, the solvent is evaporated to dryness. The residue, a yellow oil, is used in the next step without further purification. HPLC: tret=1.07 min (Grad 1); NMR (DMSO-d6): 8.15/d (1H), 7.29/s (1H), 7.26/d×d (1H), 3.92/s (3H) and 3.85/s (3H).

후처리

  1. customThe cold reaction mixture
  2. extractionis extracted with ether
  3. dry with materialAfter drying the organic phase with sodium sulfate
  4. customthe solvent is evaporated to dryness
  5. customThe residue, a yellow oil, is used in the next step without further purification
  6. customtret=1.07 min (Grad 1)

출처 및 근거

ORD 기록
ord-8852b86ea5554b2ba989a16cae449eff
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07998972B2

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