Sodium Hydroxide → 2-(Quinolin-6-yl)prop-2-enoic acid

HRID 1512074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512074
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[CH2:16])[C:12]([O:14]C)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1.O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[CH2:16])[C:12]([OH:14])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 67368576Methyl 2-(quinolin-6-yl)acrylate

Produkt 1

HCID 219927482-(Quinolin-6-yl)prop-2-enoic acidAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Accordingly, as shown in step iii of Scheme 1, methyl 2-(quinolin-6-yl)acrylate (75.0 g) was dissolved in a solution containing sodium hydroxide (65.2 g, 1.63 mol) in 1.1 liters of tetrahydrofuran and 1.1 liters of water. The reaction was stirred at room temperature overnight. The organic layer was partitioned off and the aqueous layer washed with 500 mL of toluene. The aqueous layer was then cooled with an ice bath and acidified by dropwise addition of concentrated HCl until a pH of 4.5 was achieved (about 125 mL of conc. HCl, 1.508 mol), resulting in a white precipitate. After the addition was complete, the reaction was stirred for an additional 0.5 hour at 5° C. The precipitate was collected by vacuum filtration, washed with water, washed with methyl t-butyl ether, and dried under vacuum to afford 2-(quinolin-6-yl)acrylic acid (compound 1003, 36.2 g): ESMS (M+1), 200.06; 1H NMR (300.0 MHz, DMSO-d6) δ 13.01 (1H, s), 8.91 (1H, dd, J=1.8, 4.2 Hz), 8.40 (1H, d, J=7.5 Hz), 8.07 (1H, d, J=1.8 Hz), 8.01 (1H, d, J=8.7 Hz), 7.84 (1H, dd, J=1.9, 8.9 Hz), 7.55 (1H, dd, J=1.2, 8.4 Hz), 6.39 (1H, d, J=0.9 Hz), 6.17 (1H, d, J=0.9 Hz).

Aufarbeitung

  1. dissolutionwas dissolved in a solution
  2. customThe organic layer was partitioned off
  3. washthe aqueous layer washed with 500 mL of toluene
  4. temperatureThe aqueous layer was then cooled with an ice bath
  5. additionacidified by dropwise addition of concentrated HCl until a pH of 4.5
  6. customresulting in a white precipitate
  7. additionAfter the addition
  8. stirringthe reaction was stirred for an additional 0.5 hour at 5° C
  9. filtrationThe precipitate was collected by vacuum filtration
  10. washwashed with water
  11. washwashed with methyl t-butyl ether
  12. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0690c6516717408d83afddc18878735e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217056B2

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