2-Methyl-N,N-diethylbenzamide → 3-[2-hydroxy-3-(pyrrolidin-1-yl)propyl]-2H-isoquinolin-1-one

Reaction equation

C([N:3]([CH2:13][CH3:14])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])C.[OH:15][CH:16]([CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)CC#N>>[OH:15][CH:16]([CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:14][C:13]1[NH:3][C:4](=[O:12])[C:5]2[C:6]([CH:11]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

Reactant 2

HCID 759452-Methyl-N,N-diethylbenzamide

HCID 230820883-Hydroxy-4-(pyrrolidin-1-yl)butyronitrile

Product 1

HCID 104459413-[2-hydroxy-3-(pyrrolidin-1-yl)propyl]-2H-isoquinolin-1-oneYield 3.3%

Procedure

By the reaction in the same manner as in Example 1a, using N,N-diethyl-2-methylbenzamide (1.91 g) and 3-hydroxy-4-(pyrrolidin-1-yl)butyronitrile (1.54 g), 3-[2-hydroxy-3-(pyrrolidin-1-yl)propyl]-2H-isoquinolin-1-one (0.089 g) was obtained.

Workup

customBy the reaction in the same manner as in Example 1a

Sources & evidence

ORD record: ord-c7611520908e45399b4cd20c9ab0919b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812178B2

Reaction notes

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