Potassium Nitrate → 2-Tert-butyl-5-nitroaniline

HRID 73966

반응식

HRID 73966 반응식
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])([CH3:4])([CH3:3])[CH3:2].[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[NH2:11])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 24434Potassium NitrateHCID 805742-tert-Butylaniline

생성물 1

HCID 8261032-Tert-butyl-5-nitroaniline수율 64%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
2.5 °C

실험 절차

To a cooled solution of sulfuric acid (90%, 50 mL) was added dropwise 2-tert-butyl-phenylamine (4.5 g, 30 mmol) at 0° C. Potassium nitrate (4.5 g, 45 mmol) was added in portions at 0° C. The reaction mixture was stirred at 0-5° C. for 5 min, poured into ice-water and then extracted with EtOAc three times. The combined organic layers were washed with brine and dried over Na2SO4. After removal of solvent, the residue was purified by recrystallization using 70% EtOH—H2O to give 2-tert-butyl-5-nitroaniline (3.7 g, 64%). 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J=8.7, 2.4 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.36 (d, J=8.7 Hz, 1H), 4.17 (s, 2H), 1.46 (s, 9H); HPLC ret. time 3.27 min, 10-99% CH3CN, 5 min run; ESI-MS 195.3 m/z (MH+).

후처리

  1. extractionextracted with EtOAc three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of solvent
  5. customthe residue was purified by recrystallization

출처 및 근거

ORD 기록
ord-378105a0be6248cd86bc151957c0e68f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

연결된 노트

불러오는 중…