反応 #410832

反応方程式

7-chloro-4-hydroxy-2-(4′-methylphenyl)-5,10-dihydro-2H-pyridazino[4,5-b]quinoline-1-one

acetyl chloride

2,6-lutidine

→

title compound

収率 62.0%

7-Chloro-4-acetyloxy-2-(4′-methylphenyl)-5,10-dihydro-2H-pyridazino[4,5-b]quinoline-1-one

収率 62.0%

溶媒

toluene

ether

反応条件

後処理

1. 1
   ろ過filtered in vacuo
2. 2
   洗浄The solids were washed with ether and ethyl acetate
3. 3
   その他The crude solids were triturated in warm ethyl acetate
4. 4
   温度cooled to room temperature
5. 5
   ろ過filtered in vacuo
6. 6
   その他After drying

実験手順

A 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.

出典