Dimethylformamide → HCID 86731094, compound

HRID 1844426Notes

Reaction equation

HRID 1844426 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2C(=[CH:10][CH:11]=1)NC(=O)[C:6]([OH:13])=[C:5]2[C:14]([O:16][CH2:17][CH3:18])=[O:15].O[C:20]1C(=O)N(C)C2C(C=1C(OCC)=O)=CC=CC=2.C([O-])([O-])=O.[Cs+].[Cs+].IC.[CH3:45][N:46]([CH:48]=[O:49])[CH3:47]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:45](=[CH:10][CH:11]=1)[N:46]([CH3:47])[C:48](=[O:49])[C:6]([O:13][CH3:20])=[C:5]2[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70685784HCID 70685784, compoundHCID 86731081HCID 86731081, compound

Product 1

HCID 86731094HCID 86731094, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 6-chloro-3-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylate (470 mg, 1.76 mmol), prepared following procedure described for Intermediate 16, was stirred in DMF (2 mL) at rt. Cs2CO3 (1430 mg, 4.39 mmol) was added followed by iodomethane (0.220 mL, 3.51 mmol). The resulting mixture was stirred at rt for 72 h. CH2Cl2 was added. The mixture was washed with H2O, brine, dried over MgSO4, filtered and concentrated to give an off-white solid ethyl 6-chloro-3-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxylate (527 mg, 1.78 mmol, 101% yield) as the major product. A small amount of the O-alkylated side product ethyl 6-chloro-2,3-dimethoxyquinoline-4-carboxylate was observed by LC-MS but not isolated (<5%). LC-MS (ESI) 295.9 (M+H), RT=1.97 min (Method B).

Workup

  1. washThe mixture was washed with H2O, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4d45565090a741cfb92167e378ea6005
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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