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

HRID 1693069

Reaktionsgleichung

Reaktionsgleichung von HRID 1693069
[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 methanol (4 ml) and THF (4 ml) was added 2N 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), and neutralized to pH 5˜6 by 2M aqueous hydrochloride. The formed precipitate was collected and washed with water to furnish the title compound (282 mg, 86% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ1.49 (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. customevaporated
  2. additiondiluted with water (5 ml)
  3. customThe formed precipitate was collected
  4. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-50b16a316fe84b3eb59a43992c46fb87
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158650B2

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