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

HRID 1756802

반응식

HRID 1756802 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3391eb55bb6c425283163877d6440556
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05442070

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