Methanol → 3-(5,6-Dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one

HRID 226932Notes

Reaction equation

HRID 226932 reaction equation
C(O[C:4](=[O:24])[C:5]([C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[N:17]=1)=[O:15])=[CH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.C1(OC2C=CC=CC=2)C=CC=CC=1.CO>CCCCCC.C(OCC)(=O)C>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([C:5]2[C:4](=[O:24])[C:9]3[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:7][CH:6]=2)=[O:15])=[N:17][C:18]=1[CH3:23]

Participants

6

Reactant 3

HCID 887MethanolHCID 7583Diphenyl EtherHCID 178471914HCID 178471914, compound

Product 1

HCID 577545223-(5,6-Dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-oneYield 20.3%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Compound 3d was prepared following the procedure outlined in Step 2 of Example 1 using 575 mg (1.77 mmol) of 2-(5,6-dimethyl-pyridine-3-carbonyl)-3-phenylamino-acrylic acid ethyl ester 2e, 30 mL of diphenyl ether. The reaction time was 2 h. Flash chromatography using 50-100% ethyl acetate in hexane followed by 0-30% methanol in ethyl acetate yielded 100 mg of the product 3d as off-white solid: LC-MSD, m/z for C17H14N2O2 [M+H]+: 279.4, HPLC retention time: 0.4 min.

Workup

  1. customCompound 3d was prepared

Sources & evidence

ORD record
ord-2b4bb958234c442eba12c3d8185be6d2
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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