Sodium Hydroxide → 2-Tert-butylquinoline-6-carboxylic acid

HRID 1094650

Reaktionsgleichung

Reaktionsgleichung von HRID 1094650
[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17]C)=[O:16])[CH:11]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 57458162Methyl 2-tert-butylquinoline-6-carboxylate

Produkt 1

HCID 207094322-Tert-butylquinoline-6-carboxylic acidAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-tert-butylquinoline-6-carboxylate (347 mg, 1.43 mmol) in MeOH (4 ml) and THF (4 ml) was added 2M aqueous sodium hydroxide (2 ml) at room temperature. The mixture was stirred at room temperature for 1.5 hours. Then evaporated, diluted with water (5 ml), neutralized to pH 5˜6 by 2M aqueous hydrochloride. The formed precipitate was collected, washed with water to furnish the title compound (282 mg, 86% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 1.49 (9H, s),7.62 (1H, d, J=8.8 Hz), 8.13 (1H, d, J=8.8 Hz), 8.20 (1H, d, J=8.8 Hz), 8.31-8.34 (1H, m),8.64-8.66 (1H, m) MS (ESI): m/z 230 (M+H)+.

Aufarbeitung

  1. customThen evaporated
  2. additiondiluted with water (5 ml)
  3. customThe formed precipitate was collected
  4. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-258071e2c0ca4008b4dd056b31d80531
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134004B2

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