Hydrochloric Acid → Azulene

HRID 2287488

反応式

HRID 2287488 の反応式
[C:1]1(C=O)[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[C:3](C=O)[CH:2]=1.S([O-])([O-])(=O)=O.[Mg+2].Cl.C([O-])(O)=O.[Na+]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 109761521,3-Azulenedicarboxaldehyde

生成物 1

HCID 9231Azulene収率 225.1%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒

反応条件

温度
95 °C

実験手順

1,3-Azulenedicarboxaldehyde (600 mg) is dissolved in 6.5 ml of pyridine. Magnesium sulfate (1200 mg) and N-tert-butylhydroxylammne hydrochloride (1638 mg,) is added to the solution,. The mixture is heated wit stirring to 95° C. under nitrogen and is stirred for 13 hours. Upon cooling to rt, the reaction mixture is poured into a separator flinnel containing 60 ml of CHCl3 and 60 ml of sat aq. NaHCO3. The aqueous layer is separated and washed with three 30 ml portions of CHCl3. The combined organc layers are dried over anhydrous MgSO4, filtered, and evaporated to give the bis-nitrone 34 (940 mg, 89% yield) as dark green crystals. Oxidation potential equals 0.72 V vs SCE. 1H NMR (CDCl3): 10.35 (s, 1H), 8.65 (d, 2H, J=10 Hz) 8.11 (s, 2H), 7.68 (t, 1H, J=10 Hz), 7.32 (t, 2H, J=10 Hz), 1.67 (s, 18H). 13C NMR (CDCl3): 139.9, 135.0, 134.2, 125.8, 125.6, 123.2, 120.5, 69.8, 28.4. IR (thin film): 3052, 2972, 1644, 1564, 1452, 1404, 1356, 1261, 1196, 1124, 1052, and 892 cm-1.

後処理

  1. temperatureThe mixture is heated wit
  2. stirringis stirred for 13 hours
  3. temperatureUpon cooling to rt
  4. additionthe reaction mixture is poured into a separator flinnel
  5. customThe aqueous layer is separated
  6. washwashed with three 30 ml portions of CHCl3
  7. dry with materialThe combined organc layers are dried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-6cc3a8e7005c4c7cbdec9421686d4b7a
出典データセット
uspto-grants-2000_07
特許番号
US06083988

関連ノート

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