Sodium Hydroxide → 1-Amino-5-fluoronaphthalene

HRID 723647노트

반응식

HRID 723647 반응식
[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

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 217302841-Fluoro-5-nitronaphthalene

생성물 1

HCID 217302891-Amino-5-fluoronaphthalene수율 81.2%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

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 vaccuo 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.

후처리

  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 vaccuo
  6. customto leave a residue which
  7. customwas purified by flash chromatography on silica gel eluting with 40 to 80% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-fc53b40d70074079ab4bc3bd9c813de8
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141578B2

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