Triethylamine → 2-Benzyloxy-5-cyano-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 278969Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:13]([O:20][N:21]1[C:30](=[O:31])[C:29]2[CH:32]=[C:33]([C:36]#[N:37])[C:34](Cl)=[C:27]3[C:28]=2[C:23](=[CH:24][CH:25]=[CH:26]3)[C:22]1=[O:38])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[CH2:13]([O:20][N:21]1[C:30](=[O:31])[C:29]2[CH:32]=[C:33]([C:36]#[N:37])[C:34]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:27]3[C:28]=2[C:23](=[CH:24][CH:25]=[CH:26]3)[C:22]1=[O:38])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of pyrrolidine (0.070 g, 0.98 mmol) and triethyl amine (0.11 g, 1.1 mmol) in acetonitrile (5 mL) at reflux was added 2-benzyloxy-6-chloro-5-cyano-benzo[de]isoquinoline-1,3-dione (0.20 g, 0.55 mmol, from Example A2). The reaction was heated at reflux for 20 minutes, then cooled to 0° C. The resulting precipitate was removed by filtration, washed with cold acetonitrile, and dried to give 0.15 g of the title compound.

Workup

temperatureThe reaction was heated
temperatureat reflux for 20 minutes
customThe resulting precipitate was removed by filtration
washwashed with cold acetonitrile
customdried

Sources & evidence

ORD record: ord-ae0d2dbd7d884c85838205bd650ebd24
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362181B1

Reaction notes

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