Nitric Acid → 1-(4-Fluoro-3-nitrophenyl)ethan-1-amine

HRID 58207

반응식

HRID 58207 반응식
[N+:1]([O-:4])(O)=[O:2].OS(O)(=O)=O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH2:19])[CH3:18])=[CH:13][CH:12]=1.[OH-].[Na+]>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH2:19])[CH3:18])=[CH:13][C:12]=1[N+:1]([O-:4])=[O:2]

참가 물질

5

반응물 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1230631-(4-Fluorophenyl)ethylamine

생성물 1

HCID 552831001-(4-Fluoro-3-nitrophenyl)ethan-1-amine수율 98%

실험 절차

Fuming HNO3 (0.48 ml, 10.8 mmol) was added carefully to ice bath cooled concentrated H2SO4 (3.6 ml, 68.2 mmol). To the mixture was added 1-(4-fluorophenyl)ethanamine (1.0 g, 7.2 mmol) dropwise. The reaction mixture was stirred with cooling for 50 minutes. The reaction mixture was poured into ice and basified with 3M NaOH solution (24 ml, 72.00 mmol) to about pH8.0. The alkaline solution was extracted with DCM twice. The combined organic layer was dried over Na2SO4 and evaporated to afford title compound (1.3 g, yield: 96%). 1H-NMR (400 MHz, CDCl3) δ 1.41 (d, 6H) 4.25 (q, 1H) 7.21-7.26 (m, 1H) 7.67 (ddd, 1H) 8.10 (dd, 1H)

후처리

  1. temperaturewith cooling for 50 minutes
  2. extractionThe alkaline solution was extracted with DCM twice
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-444c61759d80495580e7f0239ac9cf0b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434697B2

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