Isopropanol → Ethyl 2-(7-((3-chlorobenzyl)oxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate

HRID 513949노트

반응식

HRID 513949 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:13](=[O:24])[N:14]2C(OC(C)(C)C)=O)=[CH:9][CH:8]=1.Cl.O1CCOCC1.CC(O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:13](=[O:24])[NH:14]2)=[CH:9][CH:8]=1

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 204431481,4-Dioxane hydrochlorideHCID 90417137HCID 90417137, 화합물

생성물 1

HCID 90416764Ethyl 2-(7-((3-chlorobenzyl)oxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To crude tert-butyl 7-((3-chlorobenzyl)oxy)-3-(2-ethoxy-2-oxoethyl)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (115.7 g, 244.1 mmol) was added a 4.0 M 1,4-dioxane hydrochloride solution (200 mL, 0.8 mol) in an ice bath. After addition, the ice bath was removed and the reaction was warmed to ambient temperature. The reaction was concentrated to a yellow oil and azeotroped with toluene (2×250 mL) to furnish a brown oil. The oil was diluted in toluene (400 mL) followed by 2-propanol (400 mL). The resulting white ppt that was formed was filtered and washed with 2-propanol to furnish the desired product as a white solid. The mother liquor was concentrated to a brown solid that was triturated with 2-propanol (400 mL), filtered and washed with 2-propanol to furnish a second crop of product (38.3 g). The two crops were combined to give (50.3 g, 55%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.43 (s, 1H), 7.35-7.29 (m, 3H), 7.06 (d, J=8.3 Hz, 1H), 6.59 (dd, J=8.3, 2.4 Hz, 1H), 6.39 (d, J=2.4 Hz, 1H), 5.02 (s, 2H), 4.23-4.15 (m, 2H), 3.12-2.92 (m, 3H), 2.92-2.77 (m, 1H), 2.48 (dd, J=16.2, 7.5 Hz, 1H), 1.29 (t, J=7.1 Hz, 3H). [M+H]=374.2.

후처리

  1. additionAfter addition
  2. customthe ice bath was removed
  3. concentrationThe reaction was concentrated to a yellow oil
  4. customazeotroped with toluene (2×250 mL)
  5. customto furnish a brown oil
  6. customThe resulting white ppt that was formed
  7. filtrationwas filtered
  8. washwashed with 2-propanol

출처 및 근거

ORD 기록
ord-9c557538551f4ff188b0019412221e92
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102674B2

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