Ethanol → HCID 12421492, compound

HRID 742955Notes

Reaction equation

HRID 742955 reaction equation
[C:1]([C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[N:4]=1)#N.[OH-:16].[Na+].C(O)C.[OH2:21]>>[CH2:14]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12](=[O:13])[C:3]([C:1]([OH:21])=[O:16])=[N:4]1)[CH3:15]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 12421488HCID 12421488, compound

Product 1

HCID 12421492HCID 12421492, compound

Procedure

A solution of 25 g 3-cyano-l-ethyl-1,4-dihydro-4-oxocinnoline, 100 g sodium hydroxide, 400 ml ethanol and 100 ml water was stirred at 70° C. for 3 hr. After the removal of ethanol by evaporation, to the mixture was added conc. hydrochloric acid to precipitate crystalline materials. Precipitates were separated by filtration, washed with water, ethyl ether/ethanol and dried to yield 25.6 g of the desired compound. Mp.=206°-208° C. 1H-NMR(DMSO-d6, δ ppm) 1.48 (3H,t), 4.76 (2H,q), 7.76 (1H,t), 8.07 (1H,m), 8.19 (1H,d), 8.33 (1H,d)

Workup

  1. customAfter the removal of ethanol
  2. customby evaporation
  3. additionto the mixture was added conc. hydrochloric acid
  4. customto precipitate crystalline materials
  5. customPrecipitates
  6. customwere separated by filtration
  7. washwashed with water, ethyl ether/ethanol
  8. customdried

Sources & evidence

ORD record
ord-61aedfbc11594e5e9ce21d8d8634d3a1
Source dataset
uspto-grants-1996_09
Patent number
US05556851

Reaction notes

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