Methylamine → N~2~-Methyl-4-nitrobenzene-1,2-diamine

HRID 2213119노트

반응식

HRID 2213119 반응식
F[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1N.[CH3:12][NH2:13].C1COCC1.C(=O)([O-])[O-].[K+].[K+].C[N:26]1CCCC1=O>>[CH3:12][NH:13][C:3]1[C:2]([NH2:26])=[CH:8][CH:7]=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=1

참가 물질

6

반응물 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 677852-Fluoro-5-nitroaniline

생성물 1

HCID 21956374N~2~-Methyl-4-nitrobenzene-1,2-diamine

반응 조건

온도
120 °C

실험 절차

In a 350 mL pressure flask, 2-fluoro-5-nitroaniline (10 g, 0.064 mol), methylamine as a 2M solution in THF (65 mL, 0.13 mol) and potassium carbonate (18 g, 0.13 mol) in 1-Methyl-2-pyrrolidinone (80 mL) were combined. The flask was sealed and heated to 120 degrees C. overnight. The reaction was monitored by TLC. When reaction was judged to be complete based upon consumption of 2-fluoro-5-nitroaniline, it was cooled to room temperature and poured into 2–3 times the total reaction volume of water. When a precipitate was formed, it was filtered and dried. The product was carried on without purification. 1H NMR (300 MHz, d6DMSO) δ 7.54 (dd, J=8.79, 2.64 Hz, 1H), 7.39 (d, J=2.64 Hz, 1H), 6.41 (d, J=8.79 Hz, 1H), 6.11 (d, J=4.39 Hz, 1H), 5.07 (s, 2H), 2.83 (d, J=4.83 Hz, 3H).

후처리

  1. customThe flask was sealed
  2. customovernight
  3. customWhen reaction
  4. customto be complete based upon consumption of 2-fluoro-5-nitroaniline, it
  5. temperaturewas cooled to room temperature
  6. additionpoured into 2–3 times the total reaction volume of water
  7. customWhen a precipitate was formed
  8. filtrationit was filtered
  9. customdried
  10. customThe product was carried on without purification

출처 및 근거

ORD 기록
ord-453685f1a9514f94977ac8bcda06111e
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105530B2

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