2-Methyl-2-butene → 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxylic acid

HRID 16629

Reaktionsgleichung

Reaktionsgleichung von HRID 16629
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([CH:20]=[O:21])=[C:9]1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.[OH:28]P([O-])(O)=O.[K+].Cl([O-])=O.[Na+]>C(#N)C.C(O)(C)(C)C.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([C:20]([OH:28])=[O:21])=[C:9]1[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphate2×HCID 28382531-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde2×HCID 23668197Sodium Chlorite2×

Produkt 1

HCID 589447281-benzyl-2-methyl-5-nitro-1H-indole-3-carboxylic acidAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a suspension of 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde (Compound 50, 150 mg, 0.51 mmol) in acetonitrile (6 ml), tert-butanol (6 ml) and H2O (6 ml) was added 2-methyl-2-butene (4 ml), potassium phosphate monobasic (1.4 g, 10.2 mmol), sodium chlorite (80%, 1.15 g, 10.2 mmol). The mixture was stirred at room temperature for 20 h, more potassium phosphate monobasic (0.35 g, 2.6 mmol) and sodium chlorite (80%, 0.29 g, 2.6 mmol) were added and stirred at room temperature for 24 h. The solvent was removed under reduced pressure. The residue solid was washed with H2O (×3) and filtered, dissolved in acetone and filtered to yield 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxylic acid (Compound 51) as a yellow powder (160 mg, 100%). 1H-NMR (ACETONE-d6) δ 2.83 (s, 3 H), 5.68 (s, 2 H), 7.06-7.15 (m, 2 H), 7.25-7.41 (m, 3 H), 7.68 (d, J=9.1 Hz, 1 H), 8.10 (dd, J =9.1, 2.3 Hz, 1 H), 9.11 (d, J=2.3 Hz, 1 H).

Aufarbeitung

  1. stirringstirred at room temperature for 24 h
  2. customThe solvent was removed under reduced pressure
  3. washThe residue solid was washed with H2O (×3)
  4. filtrationfiltered
  5. dissolutiondissolved in acetone
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-7a744141b8f04f279f740449c088f55b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737173B2

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