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

HRID 1053615ノート

反応式

HRID 1053615 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 712Formaldehyde溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d2e595a6793844f59cbb933645e75d1f
出典データセット
uspto-grants-2016_07
特許番号
US09394240B2

反応ノート

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