Nitric Acid → 4-Fluoro-2-methyl-5-nitroaniline

HRID 599335

반응식

HRID 599335 반응식
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1>OS(O)(=O)=O>[F:5][C:6]1[C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 679824-Fluoro-2-methylaniline

생성물 1

HCID 190352714-Fluoro-2-methyl-5-nitroaniline수율 74%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
-10 °C

실험 절차

Concentrated nitric acid (17 g, 0.18 mol) was added dropwise to a stirred solution of 4-fluoro-2-methylaniline (20 g, 0.16 mol) in cone H2SO4 (300 mL) at −10° C. The mixture was stirred at −10° C. for 10 min., and the reaction mixture was poured into ice water. The resultant solid was collected by filtration and partitioned between EtOAc and aq Na2CO3 solution (pH 8). The organic solution was washed with brine, dried (MgSO4) and concentrated to give 4-fluoro-2-methyl-5-nitroaniline (20 g, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.27 (d, J=6.8 Hz, 1 H), 7.14 (d, J=12.4 Hz, 1 H) 5.37 (s, 2 H), 2.10 (s, 3 H).

후처리

  1. filtrationThe resultant solid was collected by filtration
  2. custompartitioned between EtOAc and aq Na2CO3 solution (pH 8)
  3. washThe organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2d38e53abfed40418e574501f432404f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897762B2

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