O-Phenylenediamine → 3-(1H-benzimidazol-2-yl)-2(1H)-Quinolinone

HRID 1017705

반응식

HRID 1017705 반응식
[O:1]=[C:2]1[C:11]([C:12](O)=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[C:15]1([NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21]>>[N:21]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:22][C:12]=1[C:11]1[C:2](=[O:1])[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

참가 물질

3

반응물 2

HCID 7243O-PhenylenediamineHCID 3324882-Quinolone-3-carboxylic acid

생성물 1

HCID 1354028533-(1H-benzimidazol-2-yl)-2(1H)-Quinolinone

실험 절차

A suspension of 2-oxo-1,2-dihydroquinoline-3-carboxylic acid 1-1 (500 mg, 2.64 mmol, 1 equiv, prepared by the method of Marsais, F; Godard, A.; Queguiner, G. J. Heterocyclic Chem. 1989, 26,1589) and 1,2-phenylenediamine (344 mg, 3.18 mmol, 1.20 equiv) in polyphosphoric acid (15 mL) was heated under argon at 200° C. for 4.5 h. The hot reaction mixture was poured over ice (200 g), and the resulting mixture was allowed to stand overnight (20 h). The precipitate was filtered, washed with water (200 mL), and air dried to give the title compound as an olive-colored solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.58 (s, 1H), 9.15 (s, 1H), 7.94 (br d, 1H, J=7.5 Hz), 7.78 (dd, 2H, J=5.6, 2.9), 7.63 (br t, 1H, J=7.5 Hz), 7.42 (br d, 1H, J=8.2 Hz), 7.33 (dd, 2H, J=5.9, 2.9), 7.25 (br t, 1H, J=7.5 Hz); HRMS (electrospray FT/ICR) calculated for C16H12N3O [M+H]+ 262.0975, found 262.0981; anal. calcd for C16H11N3O+1.10 H3PO4+0.75 H2O: C, 50.23; H, 4.16; N, 10.98. Found C, 50.24; H, 4.21; N, 10.93.

후처리

  1. customprepared by the method of Marsais, F
  2. custom(20 h)
  3. filtrationThe precipitate was filtered
  4. washwashed with water (200 mL), and air
  5. customdried

출처 및 근거

ORD 기록
ord-1f7b4d946cf540da806a36f0e3f9640b
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479512B1

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