Hydrochloric Acid → 8-(Pyridine-4-carbonyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one

HRID 44195

반응식

HRID 44195 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[Na+].[Cl-].[CH2:7]1[C:17]2=[C:18]3[C:13](=[CH:14][CH:15]=[CH:16]2)[CH2:12][CH2:11][C:10](=[O:19])[N:9]3[CH2:8]1.Cl.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.Cl>CC(C)=O.O>[N:25]1[CH:26]=[CH:27][C:22]([C:21]([C:15]2[CH:14]=[C:13]3[C:18]4=[C:17]([CH2:7][CH2:8][N:9]4[C:10](=[O:19])[CH2:11][CH2:12]3)[CH:16]=2)=[O:28])=[CH:23][CH:24]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 91665PyroquilonHCID 6451240Aluminum(III) Chloride2회HCID 12262826Isonicotinoyl chloride hydrochloride

생성물 1

HCID 444798808-(Pyridine-4-carbonyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one수율 27%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

To a molten mixture of AlCl3 (8.0 g, 60.0 mmol) and NaCl (2.34 g, 40.0 mmol) at 150° C. was added 1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one (1.79 g, 10.0 mmol) and thereafter isonicotinoylchloride hydrochloride salt (1.96 g, 11.0 mmol) portionwise. After stirring for 15 min and cooling to room temperature, excess aluminum chloride was decomposed by the addition of a chilled mixture of 10 ml concentrated hydrochloric acid and 200 ml water. Neutralization with NaHCO3 solution and subsequent extraction with ethyl acetate (3×100 ml), followed by drying over MgSO4 and removal of the solvent gave the crude product. Purification by crystallization from acetone gave the acylation product (751 mg, 2.70 mmol, 27%) as a yellow solid, mp (acetone) 184° C. 1H-NMR (500 MHz, CDCl3): δ=2.70 (t, 3J=7.7 Hz, 2H), 2.99 (t, 3J=7.8 Hz, 2H), 3.21 (t, 3J=8.2 Hz, 2H), 4.12 (t, 3J=8.2 Hz, 2H), 7.49 (m, 3H), 7.55 (s, 1H), 8.76 (d, 3J=5.1 Hz, 2H), 13C-NMR (125 MHz, CDCl3): δ=24.1, 27.2, 31.3, 45.7, 119.9, 122.6, 126.1, 129.0, 129.4, 131.4, 145.3, 146.3, 150.2, 167.8, 193.9. MS m/z 279.07 (MH+).

후처리

  1. extractionNeutralization with NaHCO3 solution and subsequent extraction with ethyl acetate (3×100 ml)
  2. dry with materialby drying over MgSO4 and removal of the solvent
  3. customgave the crude product
  4. customPurification
  5. customby crystallization from acetone

출처 및 근거

ORD 기록
ord-8070d91b038743d8858a17e37cf1cc7d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541404B2

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