O-Xylene → Phthalazine

HRID 427333

반응식

HRID 427333 반응식
O=[N:2][NH2:3].Cl.C(N(CC)CC)C.[C:12]1([CH3:19])[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=1>>[CH:18]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[N:3][N:2]=1

참가 물질

4

반응물 3

HCID 7237O-XyleneHCID 11130Triethylamine hydrochlorideHCID 37183Nitrosamine

생성물 1

HCID 9207Phthalazine수율 74%

실험 절차

1,1′-Carbonyldiimidazole (0.917 g, 5.65 mmol) was added to a stirred solution of 3-furoic acid (0.634 g, 5.65 mmol) in DMF (30 ml). The solution was stirred for 2 h before adding the preceding hydrazine (1.19 g, 5.14 mmol) and triethylamine (0.71 ml, 5.14 mmol) and triethylamine (0.71 ml, 5.14 mmol). After 18 h at room temperature, the solvent was evaporated in vacuo and water added to the residue. The resultant precipitate was collected by filtration, washed with water and hexane and dried in vacuo to give the ketohydrazine (0.66 g, 45%), MS (ES+) m/e 289 [MH]+. A solution of the ketohydrazine (0.66 g, 2.3 mmol) and triethylamine hydrochloride (0.07 g, 0.5 mmol) in xylene (40 ml) was heated at reflux for 18 h. The solution was cooled to room temperature and the solvent evaporated in vacuo. Diethyl ether was added to the residue and the resulting solid collected by filtration, washed with diethyl ether and dried in vacuo to give the title-phthalazine (0.46 g, 74%), 1H NMR (250 MHz, CDCl3) δ 7.32 (1H, d, J=1.8 Hz, Ar—H), 7.62 (1H, d, J=1.4 Hz. Ar—H), 7.90 (1H, m, Ar—H), 8.04 (1H, t, J=7.6 Hz, Ar—H), 8.31 (1H, d, J=8.2 Hz, Ar—H), 8.58 (1H, s, Ar—H), 8.75 (1H, d, Ar—H); MS (ES+) m/e 271 [MH]+.

후처리

  1. temperatureat reflux for 18 h
  2. customthe solvent evaporated in vacuo
  3. additionDiethyl ether was added to the residue
  4. filtrationthe resulting solid collected by filtration
  5. washwashed with diethyl ether
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-27d607ace67b48cb9d7c334f9f666a27
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313125B1

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