Potassium Carbonate → HCID 70914076, compound

HRID 2277431Notes

Reaction equation

HRID 2277431 reaction equation
C(O[C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]([C:17](=[O:21])[CH2:18][C:19]#[N:20])[CH2:12][CH2:13][O:14][CH2:15][CH3:16])C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.Cl>[CH2:15]([O:14][CH2:13][CH2:12][N:11]1[C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:4]([OH:22])=[C:18]([C:19]#[N:20])[C:17]1=[O:21])[CH3:16]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 70873979HCID 70873979, compound

Product 1

HCID 70914076HCID 70914076, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-[(2-Cyano-acetyl)-(2-ethoxy-ethyl)-amino]-benzoic acid ethyl ester (1 eq, 0.200 g, 0.66 mmole) in dimethylformamide (25 mL) was added potassium carbonate (1.5 eq, 0.136 g , 0.99 mmole) the resulting mixture was heated to 80° C. for 4 hours. Reaction mixture was diluted with 1N HCl aq (25 mL) and extracted with ethyl acetate (25 mL×3). Combined organic phase was washed consecutively with water, brine before, drying over sodium sulfate. Organic phase was evaporated and the residue was purified by flash chromatography to afford 1-(2-Ethoxy-ethyl)-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carbonitrile as a pale yellow solid (0.161 g, 95%, LCMS calc M+H 259, obs M+H 259).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (25 mL×3)
  3. washCombined organic phase was washed consecutively with water, brine before,
  4. dry with materialdrying over sodium sulfate
  5. customOrganic phase was evaporated
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-20081bd9a3184625baaac3aafe5184f7
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

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