Phthalimide → HCID 66605194, compound

HRID 591782Notes

Reaction equation

HRID 591782 reaction equation
O[CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[NH:13][C:14](=[O:26])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=3[O:24][CH3:25])=[CH:7][C:6]=1[CH3:27].[C:28]1(=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30](=[O:37])[NH:29]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:23][O:22][C:18]1[CH:19]=[C:20]2[C:15](=[C:16]([O:24][CH3:25])[CH:17]=1)[C:14](=[O:26])[NH:13][C:12]([C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([O:4][CH2:3][CH2:2][N:29]3[C:30](=[O:37])[C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:28]3=[O:38])=[C:6]([CH3:27])[CH:7]=1)=[CH:21]2

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 24962983HCID 24962983, compound

Product 1

HCID 66605194HCID 66605194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-6,8-dimethoxy-2H-isoquinolin-1-one (0.80 g, 2.16 mmol), isoindole-1,3-dione (0.35 g, 2.38 mmol), and triphenylphosphine (0.85 g, 3.25 mmol) in THF (30 mL), was added diethyl azodicarboxylate (0.56 g, 3.25 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The solvent was evaporated in vacuo and the residue was washed with ether to give the title compound as an off-white solid. Yield: 1.11 g (crude). 1H NMR (400 MHz, CDCl3): δ 8.34 (s, 1H), 7.89 (m, 2H), 7.77 (m, 2H), 7.21 (s, 2H), 6.49 (br s, 2H), 6.44 (s, 1H), 4.16 (m, 2H), 4.08 (m, 2H), 3.97 (s, 3H), 3.89 (s, 3H), 2.25 (s, 6H). MS (ES) m/z: 499.06 (M+1) (100%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. washthe residue was washed with ether

Sources & evidence

ORD record
ord-930c29be3a7a4453a022f9eeb74e08a5
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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