p-Aminophenylacetic acid ethyl ester → ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

HRID 15720

反応式

HRID 15720 の反応式
Br[CH2:2][C:3]1[C:12]([CH2:13]Br)=[C:11]([O:15][CH2:16][CH3:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:18][CH2:19][CH3:20].[CH2:21]([O:23][C:24](=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH3:22]>CN(C)C=O>[CH2:21]([O:23][C:24](=[O:33])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:13][C:12]3[C:11]([O:15][CH2:16][CH3:17])=[C:10]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]4=[C:4]([O:18][CH2:19][CH3:20])[C:3]=3[CH2:2]2)=[CH:30][CH:31]=1)[CH3:22]

参加物

4

反応物 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 210793342,3-Bis(bromomethyl)-1,4-diethoxy-naphthalene

生成物 1

HCID 131726211ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate収率 36%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2,3-bis(bromomethyl)-1,4-diethoxy-naphthalene (41 mg, 0.1 mmol) and 4-aminophenylacetic acid ethyl ester (20 mg, 0.11 mmol) in N,N-dimethylformamide (1 ml) was heated at 60° C. under nitrogen for 14 h. The solvent was removed in vacuo and the residue taken up in ethyl acetate (10 ml) and washed with 8% aqueous sodium bicarbonate solution (5 ml). The organic layer was dried over magnesium sulphate and the solvent removed in vacuo. Purification by flash column chromatography on silica gel eluting with 90% cyclohexane/ethyl acetate gave the product as a white solid (15 mg, 36%).

後処理

  1. customThe solvent was removed in vacuo
  2. washwashed with 8% aqueous sodium bicarbonate solution (5 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customthe solvent removed in vacuo
  5. customPurification by flash column chromatography on silica gel eluting with 90% cyclohexane/ethyl acetate

出典と根拠

ORDレコード
ord-053c8e8e62434c409462a28dcbd344c3
出典データセット
uspto-grants-2010_06
特許番号
US07732622B2

関連ノート

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