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

HRID 1017705

Reaction equation

HRID 1017705 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1f7b4d946cf540da806a36f0e3f9640b
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Linked notes

Loading…