Sodium Hydroxide → 1-Amino-5-fluoronaphthalene

HRID 2378389노트

반응식

HRID 2378389 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 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.

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 vacuo
  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-0be9ff55228e465aac0bfd06d493771d
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470797B2

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