4-Chloro-benzoic Acid 1-(4-Methoxyphenyl)hydrazide Hydrochloride → 3-(1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl)-2-methylpropanoic acid

HRID 527447ノート

反応式

HRID 527447 の反応式
[CH3:1][CH:2]([CH2:6][C:7](=O)[CH2:8][CH3:9])[C:3]([OH:5])=[O:4].Cl.[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([N:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)N)=[O:18])=[CH:15][CH:14]=1>C(O)(=O)C>[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([N:19]2[C:21]3[C:22](=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[C:8]([CH3:9])=[C:7]2[CH2:6][CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[O:18])=[CH:15][CH:14]=1

参加物

4

反応物 2

HCID 124352824-Chloro-benzoic Acid 1-(4-Methoxyphenyl)hydrazide HydrochlorideHCID 129854572-Methyl-4-oxohexanoic acid

生成物 1

HCID 716008183-(1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl)-2-methylpropanoic acid収率 44%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

2-methyl-4-oxohexanoic acid (27.6 mg, 0.19 mmol) was added to a stirred solution of 4-chloro-N-(4-methoxyphenyl)benzohydrazide hydrochloride (50 mg, 0.16 mmol) in acetic acid (0.5 mL), the mixture was heated at 80° C. under nitrogen for 3 h, then it was allowed to cool to ambient temperature and stirred overnight. Ice-water (2 mL) was poured into the cold reaction mixture and the formed precipitate was collected by filtration, carefully washed with water and dried in vacuo to yield the title compound (27 mg, 44%) as an off-white solid. C21H20ClNO4, Mr=385.84; 1H NMR (400 MHz, DMSO-d6) d: 1.01 (d, J=6.8 Hz, 3H), 2.19 (s, 3H), 2.54 (sex, J=7.2 Hz, 1H), 2.91-3.19 (m, 2H), 3.76 (s, 3H), 6.46 (d, J=9.2 Hz, 1H), 6.64 (dd, J=2.4/9.0 Hz, 1H), 7.02 (d, J=2.4 Hz, 1H); LCMS (ESI) tR: 2.78 min (>99%, ELSD), m/z: 386.1 [M+1]+.

後処理

  1. temperatureto cool to ambient temperature
  2. filtrationthe formed precipitate was collected by filtration
  3. washcarefully washed with water
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-adfe4f51a13d4a58b4fd4e3818a5a46e
出典データセット
uspto-grants-2016_05
特許番号
US09346803B2

反応ノート

読み込み中…