Water → 2-(2,6-Dichloro-phenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one

HRID 562424ノート

反応式

HRID 562424 の反応式
C(O[C:4](=O)[C:5]([C:10]1[CH:28]=[CH:27][C:13]2[N:14]=[C:15]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[N:16]([CH3:17])[C:12]=2[C:11]=1[C:29]#[N:30])(C)[C:6](=O)[CH3:7])C.O.S(=O)(=O)(O)[OH:34]>C(O)(=O)C>[Cl:25][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:26])[C:19]=1[NH:18][C:15]1[N:16]([CH3:17])[C:12]2[C:11]3[C:29](=[O:34])[NH:30][C:6]([CH3:7])=[C:5]([CH3:4])[C:10]=3[CH:28]=[CH:27][C:13]=2[N:14]=1

参加物

5

反応物 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 120354962-[4-cyano-2-(2,6-dichloro-phenylamino)-3-methyl-3H-benzoimidazol-5-yl]-2-methyl-3-oxo-butyric acid ethyl ester

生成物 1

HCID 99082472-(2,6-Dichloro-phenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one収率 46%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A 25 mL round bottom flask was charged with 2-[4-cyano-2-(2,6-dichloro-phenylamino)-3-methyl-3H-benzoimidazol-5-yl]-2-methyl-3-oxo-butyric acid ethyl ester (0.258 g, 0.562 mmol) and a stir bar. Water (3 mL), glacial acetic acid (3 mL) and concentrated sulfuric acid (3 mL) were combined and added to the round bottom flask while still hot (60° C.). The flask was sealed with a plastic stopper and heated in an oil bath at 100° C. After 2 hours, the flask was removed from the oil bath and stirred at room temperature overnight. The clear solution was then poured onto ice and neutralized with concentrated ammonium hydroxide. The resulting precipitate was recovered by filtration, resuspended in methanol and filtered. The resulting solid was washed with methanol until the filtrate was colorless to provide 2-(2,6-dichloro-phenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one (0.106 g, 46%) as a light gray solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6+TFA) δ 11.47 (s, 1H), 7.78-7.68 (m, 4H), 7.59 (t, 1H, J=8.6 Hz), 4.28 (2, 3H), 2.31 (s, 3H), 2.22 (s, 3H); ESMS (m/z): found, 387.

後処理

  1. additionadded to the round bottom flask while still hot (60° C.)
  2. customThe flask was sealed with a plastic stopper
  3. customthe flask was removed from the oil bath
  4. additionThe clear solution was then poured onto ice and neutralized with concentrated ammonium hydroxide
  5. filtrationThe resulting precipitate was recovered by filtration
  6. filtrationfiltered
  7. washThe resulting solid was washed with methanol until the filtrate

出典と根拠

ORDレコード
ord-d096d849d6a14a0eba8e6f8d14cb06f5
出典データセット
uspto-grants-2011_11
特許番号
US08067395B2

反応ノート

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