[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[N:13]=[C:12]([OH:24])[C:8]=3[NH:9][C:10]=2[CH:11]=1.[C:25](Cl)(=[O:27])[CH3:26].N1C(C)=CC=CC=1C>C1(C)C=CC=CC=1.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[N:13]=[C:12]([O:24][C:25](=[O:27])[CH3:26])[C:8]=3[NH:9][C:10]=2[CH:11]=1A suspension of the 7-chloro-4-hydroxy-2-(4′-methylphenyl)-5,10-dihydro-2H-pyridazino[4,5-b]quinoline-1-one (755 mg), acetyl chloride (0.205 mL) and 2,6-lutidine (0.337 mL) was refluxed in toluene (6 mL) for 2 hours. The resulting mixture was cooled to room temperature. The resulting paste was diluted with ether (15 mL) and filtered in vacuo. The solids were washed with ether and ethyl acetate. The crude solids were triturated in warm ethyl acetate, then cooled to room temperature and filtered in vacuo. After drying this afforded the title compound as a light yellow solid (528 mg, 62%). mp 238-240° C.; MS 382 (m+H); NMR 2.34(s,3H), 2.41(s,3H), 3.85(s, 2H), 6.98(dd,1H,J1=8.1,J2=1.9), 7.09(d,1H,J=1.9), 7.18(d,1H,J=8.1), 7.28(d,2H,J=8.3), 7.39(d,2H,J=8.3), 9.06(s,1H); Analysis C20H16ClN3O3. 0.03M H2O expected/theoretical C 62.09/62.04H 4.24/2.27 N 10.62/10.85.
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