tert-Butanol → 2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid

HRID 381766

Reaktionsgleichung

Reaktionsgleichung von HRID 381766
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:19]1[C:20](=[O:29])[NH:21]C2C(C=1)=CC=CC=2)=O)(C)(C)C.[CH3:30][C:31]([CH2:33][CH3:34])=[CH2:32].OP([O-])(O)=O.[Na+].Cl([O-])=[O:42].[Na+].[CH3:45][C:46](O)(C)C>C1COCC1>[O:29]=[C:20]1[C:19]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[CH:12][C:13]([C:17]([OH:18])=[O:42])=[CH:14][CH:15]=3)=[CH:30][C:31]2[C:32](=[CH:45][CH:46]=[CH:34][CH:33]=2)[NH:21]1

Komponenten

7

Edukt 5

HCID 6386tert-ButanolHCID 112402-Methyl-1-buteneHCID 121116895-Formyl-2-(2-oxo-1,2-dihydro-quinolin-3-yl)-indole-1-carboxylic acid tert-butyl esterHCID 23668197Sodium Chlorite2×HCID 23672064Monosodium phosphate2×

Produkt 1

HCID 226682542-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-(2-oxo-1,2-dihydro-3-quinolinyl)i1H-indole-5-carbaldehyde (5-8, 500 mg, 1.29 mmol, 1 equiv) in a 4:1 mixture of THF and t-BuOH was treated with 2 -methyl butene (8 mL), an aqueous solution of sodium phosphate monobasic (0.14 M 355.2 mg, 2.57 mmol, 2.00 equiv), and sodium chlorite (232.8 mg, 2.57 mmol, 2.00 equiv). Additional solid sodium phosphate monobasic (380 mg, 2.76 mmol, 2.14 equiv) and sodium chlorite (300 mg, 3.32 mmol, 2.57 equiv) was added in 2 equal portions over 2.5 h. The reaction mixture was concentrated, and the residue dissolved in EtOAc (60 mL), then washed twice with a 25:1 mixture of aqueous 10% sodium bisulfite solution and 10% potassium hydrogen sulfate solution (2×50 mL). The organic layer was dried over sodium sulfate, concentrated, and combined with a precipitate in the aqueous layer which was filtered and dried to 2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid (6-1) as an off-white solid. 1H NMR (500 MHz, DMSO) δ12.13 (s, 1H), 8.27 (s, 1H), 8.14 (m, 3H), 7.95 (d, 1H, J=7.8 Hz), 7.76 (d, 1H, J=7.8 Hz), 7.54 (t, 1H, J=7.8), 7.36 (d, 1H, J=7.8), 7.24 (t, 1H, J=7.8) 1.36 (s, 9H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in EtOAc (60 mL)
  3. washwashed twice with a 25:1 mixture of aqueous 10% sodium bisulfite solution and 10% potassium hydrogen sulfate solution (2×50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. filtrationwas filtered
  7. dry with materialdried to 2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid (6-1) as an off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-34b9e7618b89497b8757735dccc7a32d
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306874B1

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