Hydrochloric Acid → 3-Cyano-6-methoxy-4-phenylisoquinoline-1-carboxylic acid

HRID 639925Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]#N)=[N:8][C:7]([C:15]#[N:16])=[C:6]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-:23].[Na+].Cl.[OH2:26]>CCO>[C:15]([C:7]1[N:8]=[C:9]([C:13]([OH:26])=[O:23])[C:10]2[C:5]([C:6]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)#[N:16]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of 6-methoxy-4-phenylisoquinoline-1,3-dicarbonitrile in 25 mL EtOH was added 2(N) aq NaOH (15 mL), and the reaction was stirred at 40° C. for 2 h. Then concentrated aq HCl (18 mL) and water (29 mL) were added to the reaction mixture and heated at 100° C. for 16 h. After cooling to rt, it was extracted with DCM (4×). The combined organic layers were dried over Na2SO4 and concentrated to a tan solid (470 mg, 85%). This crude product was used without further purification.

Workup

temperatureheated at 100° C. for 16 h
temperatureAfter cooling to rt
extractionit was extracted with DCM (4×)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated to a tan solid (470 mg, 85%)
customThis crude product was used without further purification

Sources & evidence

ORD record: ord-49b7d6e1f4034879bf4c129766978f33
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691879B2

Reaction notes

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