Sodium Bicarbonate → 2-Benzyloxy-3-nitroaniline

HRID 1064843ノート

反応式

HRID 1064843 の反応式
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH2:19]([O:18][C:10]1[C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=[CH:14][C:9]=1[NH2:8])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 222727421,1-Dimethylethyl N-[3-nitro-2-(phenylmethoxy)phenyl]carbamate

生成物 1

HCID 222727492-Benzyloxy-3-nitroaniline収率 96.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

N-tert-Butoxycarbonyl-2-benzyloxy-3-nitroaniline (9.37 g, 27.2 mmol) was dissolved in methanol (150 ml), p-toluenesulfonic acid monohydrate (7.84 g, 45.5 mmol) was added thereto and the mixture was stirred at 50° C. for 12 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified by a silica gel column chromatography (50 g of silica gel; developing solvent, hexane:ethyl acetate=6:1) to provide 6.44 g (yield 96.9%) of 2-benzyloxy-3-nitroaniline as pale yellowish brown oil.

後処理

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively and dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by a silica gel column chromatography (50 g of silica gel; developing solvent, hexane:ethyl acetate=6:1)

出典と根拠

ORDレコード
ord-e7b2917423a448aabfbbb15cc96cb189
出典データセット
uspto-grants-2005_11
特許番号
US06969711B2

反応ノート

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