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Hydrochloric Acid → 8-Chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylic acid

HRID 910154
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HRID 910154 반응식
[Cl:1][C:2]1[C:11]([C:12]([O:14]C)=[O:13])=[C:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:16])[C:3]=1[F:17].[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:16])[C:3]=1[F:17]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57689813Methyl 8-chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate

생성물 1

HCID 576898038-Chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

Methyl 8-chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylate (7c, 600 mg, 2.43 mmol) was dissolved in THF (10 ml) and MeOH (5 ml). 1N NaOH (5 ml) was added and the solution stirred at RT overnight. The solution was acidified with 4N HCl then extracted into DCM and the aqueous washed ×3 with DCM. The organic portions were evaporated to give the title compound which was used without further purification (426 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.61-1.79 (m, 4H) 2.83 (t, J=6.06 Hz, 2H) 3.94 (t, J=6.32 Hz, 2H) 13.75 (br. s., 1H) [M+H] calc'd for C10H9ClFNO3, 246. found, 246.

후처리

  1. extractionthen extracted into DCM
  2. washthe aqueous washed ×3 with DCM
  3. customThe organic portions were evaporated

출처 및 근거

ORD 기록
ord-2910737c1b0143aa948e7b0c0fe401e6
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022057B2

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