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

HRID 15720

Reaction equation

HRID 15720 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-053c8e8e62434c409462a28dcbd344c3
Source dataset
uspto-grants-2010_06
Patent number
US07732622B2

Linked notes

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