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Hydrochloric Acid → 1-cyclopropyl-8-(4-methyl-phenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid

HRID 1854856
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인쇄 미리보기

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HRID 1854856 반응식
[CH:1]1([C:4]2[CH:5]=[C:6]([C:23]([O:25]CC)=[O:24])[C:7](=[O:22])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.[Li+].[OH-].Cl.C(OCC)(=O)C>C1COCC1.O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:23]([OH:25])=[O:24])[C:7](=[O:22])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:10]=[CH:9]3)[CH2:3][CH2:2]1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 23019657ethyl 1-cyclopropyl-8-(4-methylphenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

생성물 1

HCID 211044531-cyclopropyl-8-(4-methyl-phenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

A solution of ethyl 1-cyclopropyl-8-(4-methylphenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (90 mg, 0.249 mmol) in THF (6 mL) and water (2 mL) was treated with LiOH (43 mg, 1.02 mmol). The reaction was heated to 60° C. for 2 h and acidified with 1N HCl to pH 4. The precipitate was dissolved with ethyl acetate (20 mL) and washed with brine (20 mL). The organic phase was separated, dried, and concentrated. The precipitate was filtered to afford the title compound EXAMPLE 33 as a yellow solid (65 mg, 78%). ESI-MS m/z: 334 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.31 (d, J=7.2 Hz, 1H), 8.24 (s, 1H), 7.54 (d, J=7.2 Hz, 1H), 7.44 (d, J=7.2 Hz, 2H), 7.38 (d, J=7.2 Hz, 2H), 2.84 (s, 3H), 2.54-2.52 (m, 1H), 2.39 (s, 3H), 1.06-1.03 (m, 2H), 0.77-0.75 (m, 2H).

후처리

  1. washwashed with brine (20 mL)
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. filtrationThe precipitate was filtered

출처 및 근거

ORD 기록
ord-d32b1a2035a143928c6aaa7fe828a1b2
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08962842B2

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