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

HRID 15720

반응식

HRID 15720 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-053c8e8e62434c409462a28dcbd344c3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732622B2

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