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

HRID 1756802

Reaction equation

HRID 1756802 reaction equation
C(O[C:4]([C:6]1[C:7]([N:18]([CH3:23])[CH2:19][CH2:20][C:21]#[N: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-])(C)C.[K+].C(O)(=O)C.C(O)C.O>O1CCCC1>[C:21]([CH:20]1[CH2:19][N:18]([CH3:23])[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])#[N:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 189946093-ethoxycarbonyl-6,7-difluoro-2-(N-methyl-N-beta-cyanoethylamino)quinolineHCID 19096565Water ethanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 189945913-Cyano-7,8-difluoro-1-methyl-4-oxo-1,2,3,4-tetrahydrobenzo[b][1,8]naphthyridineYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 19.17 g of 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(b-cyanoethyl)amino]quinoline in 50 cm3 of tetrahydrofuran is introduced in the course of 60 minutes into a solution, cooled to -10° C. of 8.74 g of potassium tert-butylate in 200 cm3 of tetrahydrofuran. The suspension obtained is stirred, still at -10° C., for a further 30 minutes 4 cm3 of glacial acetic acid are then introduced. The tetrahydrofuran is evaporated off under reduced pressure (20 pKa). The crude reaction mixture is taken up with 200 cm3 of an aqueous-alcoholic ethanol/water (70/30 vol/vol) mixture. The precipitate obtained is filtered off, washed twice with 50 cm3 of water and then dried under reduced pressure (20 kPa). 16.1 g of 3--cyano-7,8-difluoro-1-methyl-4-oxo-1,2,3,4-tetrahydrobenzo[b][1,8]naphthyridine are isolated in the form of a golden-yellow solid, melting point 144° C.

Workup

  1. customThe suspension obtained
  2. additionare then introduced
  3. customThe tetrahydrofuran is evaporated off under reduced pressure (20 pKa)
  4. customThe crude reaction mixture
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. washwashed twice with 50 cm3 of water
  8. customdried under reduced pressure (20 kPa)

Sources & evidence

ORD record
ord-3391eb55bb6c425283163877d6440556
Source dataset
uspto-grants-1995_08
Patent number
US05442070

Linked notes

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