Hydrochloric Acid → HCID 131725821, compound

HRID 1833261Notes

Reaction equation

HRID 1833261 reaction equation
[ClH:1].C(OC1C=C(C=CC=1)C(C1C2C(=CC(OC)=C(OC)C=2)C(C#N)=CN=1)=O)C.C([O:31][C:32]([C:34]1[C:43]2[C:38](=[CH:39][C:40]([O:46][CH3:47])=[C:41]([O:44][CH3:45])[CH:42]=2)[C:37]([C:48](=[O:58])[C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([O:55][CH2:56][CH3:57])[CH:50]=2)=[N:36][CH:35]=1)=[NH:33])C.C(OC1C=C(C=CC=1)C(C1C2C(=CC(OC)=C(OC)C=2)C(C(N)=O)=CN=1)=O)C>C(O)C>[ClH:1].[CH2:56]([O:55][C:51]1[CH:50]=[C:49]([CH:54]=[CH:53][CH:52]=1)[C:48]([C:37]1[C:38]2[C:43](=[CH:42][C:41]([O:44][CH3:45])=[C:40]([O:46][CH3:47])[CH:39]=2)[C:34]([C:32]([NH2:33])=[O:31])=[CH:35][N:36]=1)=[O:58])[CH3:57]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 11314999HCID 11314999, compoundHCID 21034880HCID 21034880, compoundHCID 220484311-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile

Product 1

HCID 131725821HCID 131725821, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The dry hydrogen chloride gas was passed to the suspension of 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile (200 mg, 0.55 mmol) in ethanol (5 mL) at 0° C. until the solution was saturated. The mixture was stirred at room temperature for 12 h. After removal of solvent and hydrogen chloride, ether was added to solidify the product. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 0%–5% methanol in methylenechloride in 30 min) afforded two products: 1st product, 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carboximidic acid ethyl ester with hydrochloride as a solid. LC-MS m/e calcd for C23H24N2O5 (MH+) 409, found 409. 1H NMR (300 MHz) compatible; 2nd product, 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid amide with hydrochloride as a solid. LC-MS m/e calcd for C21H20N2O5 (MH+) 381, found 381. 1H NMR (300 MHz) compatible.

Workup

  1. customAfter removal of solvent and hydrogen chloride, ether
  2. additionwas added
  3. customFlash chromatography (Merck Silica gel 60, 70–230 mesh, 0%–5% methanol in methylenechloride in 30 min) afforded two products

Sources & evidence

ORD record
ord-671fad0f940d408cbea8e4290148eff9
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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