Acetic Acid → 2-(4-Cyano-benzyl)-3-hydroxy-7,8,9,10-tetrahydro-benzo[h]quinoline-4-carboxylic Acid

HRID 2375574ノート

反応式

HRID 2375574 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH2:13][CH2:12][CH2:11][CH2:10][C:8]3=2)[C:3](=O)[C:2]1=[O:15].[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](=O)COC(=O)C)=[CH:20][CH:19]=1)#[N:17].[C:32]([OH:35])(=[O:34])C>C(O)C.[OH-].[Na+]>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:2]([OH:15])=[C:3]([C:32]([OH:35])=[O:34])[C:4]3[C:9](=[C:8]4[CH2:10][CH2:11][CH2:12][CH2:13][C:7]4=[CH:6][CH:5]=3)[N:1]=2)=[CH:20][CH:19]=1)#[N:17]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 12339563Acetic Acid 3-(4-cyano-phenyl)-2-oxo-propyl EsterHCID 137804146,7,8,9-Tetrahydro-1H-benzo[g]indole-2,3-dione

生成物 1

HCID 112220682-(4-Cyano-benzyl)-3-hydroxy-7,8,9,10-tetrahydro-benzo[h]quinoline-4-carboxylic Acid収率 20%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 14798Sodium Hydroxide溶媒

実験手順

In a 25 mL round-bottomed flask, 6,7,8,9-tetrahydrobenzo[g]indoline-2,3-dione (0.119 g, 0.590 mmol) was taken up in 1 mL ethanol and 3 mL 10 M NaOH, and the mixture heated at reflux temperature for 3 minutes. A solution of acetic acid 3-(4-cyano-phenyl)-2-oxo-propyl ester (0.167 g, 0.767 mmol) in 3 mL ethanol was then added and the reaction further heated for 10 minutes. The reaction mixture was then cooled to room temperature and acidified with glacial acetic acid, and the yellow precipitate collected by filtration. The procedure described above for the purification of example 7 was followed. Product was obtained as a bright yellow powder (42 mg, 20% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 1.74-1.87 (m, 4H) 2.83 (t, J=5.31 Hz, 2H) 3.12 (t, J=5.43 Hz, 2H), 4.40 (s, 2H), 7.28 (d, J=9.09 Hz, 1H) 7.51 (d, J=8.59 Hz, 2H) 7.75 (d, J=8.34 Hz, 2H) 8.23 (d, J=8.84 Hz, 1H).

後処理

  1. temperatureat reflux temperature for 3 minutes
  2. customthe reaction
  3. temperaturefurther heated for 10 minutes
  4. filtrationthe yellow precipitate collected by filtration
  5. customThe procedure described above for the purification of example 7

出典と根拠

ORDレコード
ord-54a8668a1b9d4c40a3b9f49b26c10368
出典データセット
uspto-grants-2008_12
特許番号
US07465798B2

反応ノート

読み込み中…