Hydrochloric Acid → 2-(Pyrrolidin-1-yl)-5-(trifluoromethyl)aniline

HRID 2099077ノート

反応式

HRID 2099077 の反応式
Cl.[Sn](Cl)Cl.[N+:5]([C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)([O-])=O.C(=O)([O-])O.[Na+]>CO>[NH2:5][C:8]1[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:10][C:9]=1[N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 27757531-[2-Nitro-4-(trifluoromethyl)phenyl]pyrrolidine

生成物 1

HCID 5187512-(Pyrrolidin-1-yl)-5-(trifluoromethyl)aniline収率 102.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Concentrated hydrochloric acid (1.36 ml, 16.3 mmol) and anhydrous tin dichloride (1.55 g, 8.16 mmol) were sequentially added at 0° C. to a methanol (4 ml) solution of 1-[2-nitro-4-(trifluoromethyl)phenyl]pyrrolidine (606 mg, 2.33 mmol), obtained as described in Referential Example 3-1. The resulting mixture was stirred for four hours. A saturated solution of sodium hydrogen carbonate was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50 g, hexane/ethyl acetate=15/1). Thus, 1-[2-amino-4-(trifluoromethyl)phenyl]pyrrolidine (550 mg, quant.) was yielded as a red-orange colored oily material.

後処理

  1. customobtained
  2. extractionthe resulting mixture was extracted three times with ethyl acetate
  3. washThe obtained organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (50 g, hexane/ethyl acetate=15/1)

出典と根拠

ORDレコード
ord-03d3663cd4ee4502a02e053869c12674
出典データセット
uspto-grants-2009_08
特許番号
US07569536B2

反応ノート

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