Water → 7-Hydroxy-6-methoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 370043Notes

Reaction equation

HRID 370043 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16]C)[CH:14]=2)[C:9](=[O:20])[CH2:8][CH:7]1[CH3:21])=[O:5])[CH3:2].[C-]#N.[Na+].O.[Cl-].[NH4+]>CS(C)=O>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([OH:16])[CH:14]=2)[C:9](=[O:20])[CH2:8][CH:7]1[CH3:21])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 15480676ethyl 6,7-dimethoxy-2-methyl-4-oxo-3,4-dihydro-1(2H)-quinolinecarboxylate

Product 1

HCID 544378587-Hydroxy-6-methoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 6,7-dimethoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (10.0 g, 34.1 mmol) and sodium cyanide (8.35 g, 170 mmol) in dimethylsulfoxide (35 mL) was heated at 130° C. for 16 h. Water (100 mL) was added, the mixture was saturated with ammonium chloride, and then extracted with ethyl acetate (4×100 mL). The combined organic extracts were washed with saturated sodium bicarbonate solution (50 mL), brine (25 mL), dried over sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 0-50% ethyl acetate/hexanes as eluent afforded the title compound (5.10 g, 54%).

Workup

  1. extractionextracted with ethyl acetate (4×100 mL)
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate solution (50 mL), brine (25 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-e9c9969b46fb4079820f78c6956e8efb
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

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