Dimethylacetamide → HCID 68993145, compound

HRID 2196595Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][N:17](C)C(=O)C>[C-]#N.[Zn+2].[C-]#N.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[C:16]#[N:17]

Participants

Conditions

Temperature: 150 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (2.0 g, 9.0 mmol) was dissolved in N,N-dimethylacetamide (12 ml). The mixture was degassed under nitrogen. Zinc(II) cyanide (0.66 g, 5.8 mml), zinc (0.084 g, 1.3 mmol), tris(dibenzylidene-acetone)dipalladium(0) (0.17 g, 0.19 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.23 g, 0.41 mmol) were then added. The reaction mixture was heated in a microwave at 150° C. for 10 minutes. The solvent was removed and the residue was purified by silica gel chromatography (hexane to ethyl acetate) to give 6,7-dimethoxyquinoline-4-carbonitrile that was dissolved in 5% hydrochloric acid (conc) in ethanol and stirred under a hydrogen balloon with Pd/C (cat.). After filtration through celite, the filtrate was collected and concentrated to give (6,7-dimethoxyquinolin-4-yl)methanaminium chloride. MS (ESI, pos. ion) m/z: 219 (M+1).

Workup

customThe mixture was degassed under nitrogen
customThe solvent was removed
customthe residue was purified by silica gel chromatography (hexane to ethyl acetate)

Sources & evidence

ORD record: ord-4521567e36924263b2263980cfcd0f1f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338455B2

Reaction notes

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