Sulfuric Acid → Methyl 2-fluoro-3-(methylamino)benzoate

HRID 1053615노트

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HRID 1053615 반응식
Cl.[NH2:2][C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].S(=O)(=O)(O)O.[C:19](=O)(O)[O-].[Na+]>C=O>[F:13][C:4]1[C:3]([NH:2][CH3:19])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67167731Methyl 3-amino-2-fluorobenzoate hydrochloride

생성물 1

HCID 58298671Methyl 2-fluoro-3-(methylamino)benzoate수율 38%

시약·촉매·용매 1

HCID 712Formaldehyde용매

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온도
40 °C

실험 절차

Methyl 3-amino-2-fluorobenzoate hydrochloride (18.65 g, 0.09 mol) was dissolved in a 37% formalin solution. While maintaining the temperature at 40° C. or lower, 98% sulfuric acid (680.81 g, 6.80 mol) was added dropwise thereto. Thereafter, the mixture was naturally cooled, and agitated for 2 hours at room temperature. The reaction mixture was poured into ice water, and was neutralized with sodium bicarbonate. The neutralized liquid was filtered, and washed with ethyl acetate. Then, the filtrate was extracted, and dried over anhydrous sodium sulfate. The sodium sulfate was filtered away, and then the concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/4), as a result of which 6.27 g (yield: 38%) of the indicated compound was obtained.

후처리

  1. temperatureThereafter, the mixture was naturally cooled
  2. filtrationThe neutralized liquid was filtered
  3. washwashed with ethyl acetate
  4. extractionThen, the filtrate was extracted
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe sodium sulfate was filtered away
  7. customthe concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/4)

출처 및 근거

ORD 기록
ord-d2e595a6793844f59cbb933645e75d1f
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394240B2

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