Sodium Hydroxide → 1-Amino-5-fluoronaphthalene

HRID 966881ノート

反応式

HRID 966881 の反応式
[F:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.[Fe]>[NH2:12][C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][CH:8]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 217302841-Fluoro-5-nitronaphthalene

生成物 1

HCID 217302891-Amino-5-fluoronaphthalene収率 81.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

A solution of compound 208A (62 mg, 0.32 mmol) in 1 mL EtOH containing 0.1 mL 12 N HCl was heated to reflux. Iron powder (62 mg, 1.11 mmol) was added in small portions and heating was continued for 2 h. The mixture was cooled, neutralized with 1 N NaOH solution and the aqueous layer was extracted with CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated in vacuo to leave a residue which was purified by flash chromatography on silica gel eluting with 40 to 80% EtOAc in hexanes to give 42 mg (0.26 mmol, 80%) of compound 208B as a yellow solid.

後処理

  1. temperatureheating
  2. temperatureThe mixture was cooled
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto leave a residue which
  7. customwas purified by flash chromatography on silica gel eluting with 40 to 80% EtOAc in hexanes

出典と根拠

ORDレコード
ord-77a22b4aaa9c49309bfa7e3fda7fe745
出典データセット
uspto-grants-2005_10
特許番号
US06953679B2

反応ノート

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