Sulfuric Acid → 6,7-Dimethoxy-1-oxo-1,2-dihydroisoquinoline-4-carbonitrile

HRID 1833238Notes

Reaction equation

C([O:3][C:4](=O)[NH:5][CH:6]=[C:7]([C:18]#[N:19])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)C.S(=O)(=O)(O)O>C1(OC2C=CC=CC=2)C=CC=CC=1.C(OCC)C>[CH3:17][O:16][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][C:11]=1[O:14][CH3:15])[C:4](=[O:3])[NH:5][CH:6]=[C:7]2[C:18]#[N:19]

Participants

Conditions

Temperature: 230 °C

Procedure

To a stirred solution of [2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-carbamic acid ethyl ester (8 g, 29.0 mmol) in diphenyl ether (70 mL) was added concentrated sulfuric acid (0.5 mL). The reaction mixture was heated at 230° C. for 4 hrs, cooled and diluted with diethyl ether (400 mL). A brown solid was precipitated, filtered, collected and washed with diethyl ether to afford 6,7-dimethoxy-1-oxo-1,2-dihydro-isoquinoline-4-carbonitrile. (3.5 g, 52% yield).

Workup

temperaturecooled
customA brown solid was precipitated
filtrationfiltered
customcollected
washwashed with diethyl ether

Sources & evidence

ORD record: ord-b7f578a8c3de432bbb86adebb6761034
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067529B2

Reaction notes

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