Hydrochloric Acid → HCID 10317161, compound

HRID 727774Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]([CH2:16][C:17]#[N:18])[C:6]1=[O:19])=[O:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].Cl>O.CN(C=O)C>[CH3:32][C:31]([O:30][C:28](=[O:29])[CH2:27][C:5]1([C:3]([O:2][CH3:1])=[O:4])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]([CH2:16][C:17]#[N:18])[C:6]1=[O:19])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 2-(cyanomethyl)-1,2,3,4-tetrahydro-1,3-dioxo-4-isoquinoline carboxylic acid methyl ester (6.5 g, 25.19 mmol), K2CO3 (6.95 g, 50.38 mmol) and anhydrous DMF (100 mL) was added tert-butyl bromoacetate (6.1 mL, 37.79 mmol). After stirring at 85° C. for 3 hours, the mixture was poured into H2O, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexane/EtOAc 4/1) gave a white solid (8.5 g, 90.7%).

Workup

extractionextracted with EtOAc
dry with materialThe organic extracts were dried over MgSO4
customEvaporation and purification by flash chromatography on silica gel (hexane/EtOAc 4/1)

Sources & evidence

ORD record: ord-6d7e4fdebcf542a0b9d1290c15e7b7e1
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05045544

Reaction notes

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