Water → 3-Methoxy-2-nitroaniline

HRID 422312

反応式

HRID 422312 の反応式
C([N:3](CC)CC)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[CH3:27][O:28][C:29]1[C:30]([N+:38]([O-:40])=[O:39])=[C:31]([CH:35]=[CH:36][CH:37]=1)C(O)=O.O>C1(C)C=CC=CC=1>[CH3:27][O:28][C:29]1[C:30]([N+:38]([O-:40])=[O:39])=[C:31]([NH2:3])[CH:35]=[CH:36][CH:37]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 786323-Methoxy-2-nitrobenzoic acidHCID 123414Diphenylphosphoryl azide

生成物 1

HCID 104647003-Methoxy-2-nitroaniline収率 35%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Triethylamine (6.29 mL) and diphenyl azidophosphate (6.66 mL, 30.1 mmol) were added to a suspension of 3-methoxy-2-nitrobenzoic acid (3.06 g, 15.2 mmol) in toluene (50 mL). The reaction mixture was stirred under reflux for 2 hours, water (10 mL) was added and it was stirred overnight under reflux. After evaporation of the solvent, the residue was dissolved in AcOEt and the resulting solution was filtered through celite. The organic phase was washed with saturated solution of NaHCO3, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 900 mg (5.35 mmol, 35%) of 3-methoxy-2-nitrophenylamine as a yellow solid.

後処理

  1. temperatureunder reflux for 2 hours
  2. stirringit was stirred overnight
  3. temperatureunder reflux
  4. customAfter evaporation of the solvent
  5. dissolutionthe residue was dissolved in AcOEt
  6. filtrationthe resulting solution was filtered through celite
  7. washThe organic phase was washed with saturated solution of NaHCO3, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1)

出典と根拠

ORDレコード
ord-02c42d74a1fb4ea68414fbb86b725ab4
出典データセット
uspto-grants-2012_01
特許番号
US08101637B2

関連ノート

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