Hydrochloric Acid → 3-(Formylamino)-3,4-dihydro-2(1H)quinolinone

HRID 1648306

Reaction equation

HRID 1648306 reaction equation
[OH-].[Na+].[CH:3]([NH:5][C:6]1(C(OCC)=O)[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:16])=[O:4].O.Cl>CO>[CH:3]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:16])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19919309Ethyl 3-(formylamino)-1,2,3,4-tetrahydro-2-oxo-3-quinolinecarboxylate

Product 1

HCID 179327143-(Formylamino)-3,4-dihydro-2(1H)quinolinoneYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (50 mL of 4.0 N, 0.20 mol) was added to a stirred solution of ethyl 3-(formylamino)-1,2,3,4-tetrahydro-2-oxo-3-quinolinecarboxylate (11.3 g, 0.043 mol) in methanol (250 mL). After 30 minutes, a white precipitate appeared and, after 45 minutes water (50 mL) was added to the reaction. After refluxing overnight, hydrochloric acid (50 mL of 4.0 N, 0.20 mol) was added and the solvents were removed under reduced pressure. The residual solid was refluxed in ethanol (200 mL) for 1 hour, filtered to remove salt, and cooled to afford 6.8 g of product, mp 197°-200° C. Anal. Calc'd for C10H10N2O2 : C, 63.15; H, 5.30; N, 14.73. Found: C, 63.03; H, 5.37; N, 14.71.

Workup

  1. waita white precipitate appeared and, after 45 minutes
  2. temperatureAfter refluxing overnight
  3. customthe solvents were removed under reduced pressure
  4. temperatureThe residual solid was refluxed in ethanol (200 mL) for 1 hour
  5. filtrationfiltered
  6. customto remove salt
  7. temperaturecooled

Sources & evidence

ORD record
ord-f794fc3745bf4307b14228c45cb6bf7b
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Linked notes

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