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

HRID 44196

反応式

HRID 44196 の反応式
[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][CH:25]=[N:24][CH:23]=1.Cl>C(O)C.O>[N:24]1[CH:25]=[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]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 91665PyroquilonHCID 6451240Aluminum(III) Chloride2 回

生成物 1

HCID 444798818-(Pyridine-3-carbonyl)-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one収率 22.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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 nicotinoylchloride 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 ethanol gave the acylation product (624 mg, 2.24 mmol, 22%) as a yellow solid, mp (ethanol) 147° C. 1H-NMR (500 MHz, CDCl3): δ=2.72 (t, 3J=7.9 Hz, 2H), 3.02 (t, 3J=7.9 Hz, 2H), 3.23 (t, 3J=8.6 Hz, 2H), 4.14 (t, 3J=8.6 Hz, 2H), 7.44 (ddd, 3J=7.9 Hz, 3J=4.7 Hz, 5J=1.0 Hz, 1H), 7.53 (s, 1H), 7.58 (s, 1H), 8.06 (m, 1H), 8.78 (dd, 3J=5.0 Hz, 4J=1.9 Hz, 1H), 8.92 (dd, 4J=1.9 Hz, 5J=0.8 Hz, 1H). 13C-NMR (125 MHz, CDCl3): δ=24.2, 27.3, 31.4, 45.8, 199.9, 123.4, 126.1, 128.9, 129.4, 132.3, 134.0, 137.0, 146.1, 150.4, 152.4, 167.8, 193.6. MS m/z 278.79 (MH+).

後処理

  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 ethanol

出典と根拠

ORDレコード
ord-65f42044164a4c2e93c4763e6f251c5c
出典データセット
uspto-grants-2013_09
特許番号
US08541404B2

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