Triethylamine → Ethyl 4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

HRID 335387노트

반응식

HRID 335387 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:18]([F:21])([F:20])[F:19])=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17].C(N(CC)CC)C>[Pd].C(O)C>[O:17]=[C:7]1[C:6]2[C:11](=[CH:2][CH:3]=[CH:4][C:5]=2[C:18]([F:19])([F:20])[F:21])[NH:10][CH:9]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 13337379Ethyl 8-chloro-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

생성물 1

HCID 21829730Ethyl 4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
5 °C

실험 절차

A 3-neck, 5 L flask was charged with of ethyl 8-chloro-4-oxo-5-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate (6A) (100 g, 0.3 mol), ethanol (1250 mL, 12.5 mL/g) and triethylamine (220 mL, 1.6 mol). The vessel was then charged with 10 g of 10% Pd/C (50% wet) at 5° C. The reaction was stirred vigorously under hydrogen atmosphere for 20 h at 5° C., after which time the reaction mixture was concentrated to a volume of approximately 150 mL. The product, ethyl 4-oxo-5-(trifluoromethyl)-1H-quinoline-3-carboxylate (6C), as a slurry with Pd/C, was taken directly into the next step.

후처리

  1. concentrationafter which time the reaction mixture was concentrated to a volume of approximately 150 mL

출처 및 근거

ORD 기록
ord-b85e20b1ba3c44eb82be0d55727fadb3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884018B2

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