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Hydrochloric Acid → [1-(4-methoxy-benzyl)-3-methyl-1H-indol-6-yl]-phenyl methanone

HRID 380407
ノート
印刷プレビュー

反応式

HRID 380407 の反応式
CON(C)[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:24])=[CH:11][N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:8][CH:7]=1)=[O:5].[C:26]1([Mg]Cl)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>O1CCCC1>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[C:13]3[C:9](=[CH:8][CH:7]=[C:6]([C:4]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:5])[CH:14]=3)[C:10]([CH3:24])=[CH:11]2)=[CH:17][CH:18]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 22663398N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamideHCID 178478979HCID 178478979、化合物

生成物 1

HCID 22663420[1-(4-methoxy-benzyl)-3-methyl-1H-indol-6-yl]-phenyl methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A stirred solution of N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamide (2.215 g, Example 25) in tetrahydrofuran (55 ml) was treated with a solution of phenylmagnesium chloride in tetrahydrofuran (9.83 ml, 2M). The solution was stirred at 0° C. for 2 hours then poured into a mixture of ice and 1N hydrochloric acid (10 ml) and then partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2, v/v) to yield the title compound (2.05 g) as a yellow solid, m.p. 146-147° C. [Elemental analysis:—C,80.80; H,6.00; N,3.80%. Calculated for C24H21NO2:—C,81.10; H,5.96; N,3.94%].

後処理

  1. custompartitioned between ethyl acetate (50 ml) and water (50 ml)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customthen evaporated
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2

出典と根拠

ORDレコード
ord-8d5d43353a164b3b8ac7bf9b9a9f43aa
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06303600B1

反応ノート

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