Phthalimide → 2-(Quinolin-6-ylmethyl)isoindoline-1,3-dione

HRID 1892283

Reaction equation

[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:31]1[C:40]2[C:35](=[CH:36][C:37]([CH2:41]O)=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>C1COCC1>[N:31]1[C:40]2[C:35](=[CH:36][C:37]([CH2:41][N:2]3[C:3](=[O:10])[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:1]3=[O:11])=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of isoindoline-1,3-dione (6.47 g, 44.0 mmol) and triphenylphosphine (11.53 g, 44.0 mmol) in THF (70 mL) at 0° C. was added a solution of quinolin-6-ylmethanol (7 g, 44.0 mmol) in THF (30 mL) and (E)-diisopropyl diazene-1,2-dicarboxylate (8.89 g, 44.0 mmol) dropwise over a period of 30 min. The mixture was heated at 30° C. and kept stirring for 20 h. After cooling and concentration, the resulting residue was purified by Analogix silica gel with gradient hexanes/EtOAc to provide 2-(quinolin-6-ylmethyl)isoindoline-1,3-dione (12.04 g, 95%). LCMS (method A): [MH]+=289, tR=4.89 min.

Workup

temperatureAfter cooling
concentrationconcentration
customthe resulting residue was purified by Analogix silica gel with gradient hexanes/EtOAc

Sources & evidence

ORD record: ord-4f359d54a6d64c6d929eed43ec45a9f1
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507676B2

Linked notes

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