Acetic Acid → 3-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,2,3,4-tetrahydrobenzo[b][1,8]naphthyridine

HRID 1756794Notes

Reaction equation

HRID 1756794 reaction equation
C(O[C:4]([C:6]1[C:7]([N:18]([CH3:26])[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([F:16])=[C:11]([F:17])[CH:10]=2)=[O:5])C.CC[O-].[Na+].C(O)(=O)C.O>C(O)C>[CH2:24]([O:23][C:21]([CH:20]1[CH2:19][N:18]([CH3:26])[C:7]2[N:8]=[C:9]3[CH:10]=[C:11]([F:17])[C:12]([F:16])=[CH:13][C:14]3=[CH:15][C:6]=2[C:4]1=[O:5])=[O:22])[CH3:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2723922Sodium ethoxideHCID 117282483-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(beta-ethoxycarbonylethyl)amino]quinoline

Product 1

HCID 98835423-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,2,3,4-tetrahydrobenzo[b][1,8]naphthyridineYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 94 g of 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(b-ethoxycarbonylethyl)amino]quinoline in 300 cm3 of absolute ethanol is added in the course of 80 minutes to a solution of 26.6 g of sodium ethylate brought to reflux in 900 cm3 of absolute ethanol. The suspension obtained, still refluxing, is stirred for a further 15 minutes. 38 cm3 of glacial acetic acid are then introduced in the course of 30 minutes. The reaction mixture is stirred for a further 15 minutes and, with the mixture still refluxing, 500 cm3 of water are then introduced in the course of 45 minutes. The suspension obtained is cooled to approximately 20° C. The precipitate is drained at approximately 20° C. and washed with twice 300 cm3 of water. The wet product is dried under reduced pressure (20 kPa) at approximately 60° C. 71.5 g of 3-ethoxycarbonyl-7,8-difluoro-1-methyl- 4-oxo-1,2,3,4-tetrahydro-benzo[b][1,8]naphthyridine are isolated in the form of a yellow solid, melting point 188° C.

Workup

  1. customThe suspension obtained
  2. temperaturestill refluxing
  3. stirringThe reaction mixture is stirred for a further 15 minutes and, with the mixture
  4. temperaturestill refluxing
  5. customThe suspension obtained
  6. customis drained at approximately 20° C.
  7. washwashed with twice 300 cm3 of water
  8. customThe wet product is dried under reduced pressure (20 kPa) at approximately 60° C

Sources & evidence

ORD record
ord-15892ffbcdd44b92a64ebe91fdf7fc63
Source dataset
uspto-grants-1995_08
Patent number
US05442070

Reaction notes

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