Sodium hydride → HCID 67250969, compound

HRID 2192032Notes

Reaction equation

HRID 2192032 reaction equation
C(O[C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH2:16])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])C.[H-].[Na+].[N-:19]=[C:20]=[O:21].[N-]=C=S>CN(C=O)C.O>[NH:16]1[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[C:4](=[O:5])[NH:19][C:20]1=[O:21]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 105034IsocyanateHCID 4570951Ethyl 4-aminoquinoline-3-carboxylateHCID 178418790HCID 178418790, compound

Product 1

HCID 67250969HCID 67250969, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of a 4-amino-quinoline-3-carboxylic acid ethyl ester derivative (0.50 mmol) in 10 mL anhydrous DMF is added sodium hydride (4 eq., 2.0 mmol) and stirred at room temperature for 30 min. To this solution an isocyanate or isothiocyanate (1.5-4 eq. 2.0 mmol) is added. The resulting reaction mixture is stirred for 18 h at room temperature or at 100° C. After completion of the reaction, the mixture is poured into water (20 mL) and extracted with ethyl acetate (2×25 mL). The organic extracts are combined, washed with water (2×25 mL), brine (2×25 mL), dried over Na2SO4 and concentrated in vacuo to give the crude product. The residue is then purified by silica gel chromatography using dichloromethane-ethyl acetate to provide desired 1H-pyrimido[5,4-c]quinoline-2,4-dione or thio-ketone derivative.

Workup

  1. customThe resulting reaction mixture
  2. stirringis stirred for 18 h at room temperature or at 100° C
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. washwashed with water (2×25 mL), brine (2×25 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customThe residue is then purified by silica gel chromatography

Sources & evidence

ORD record
ord-59a3a70874794657953c19b37781c39e
Source dataset
uspto-grants-2012_12
Patent number
US08329715B2

Reaction notes

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