Acetic Acid → 1-Ethyl-3-hydroxy-5-methyl-3-(3,4,5-trimethoxybenzyl)indolin-2-one

HRID 1523079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523079
C([O:9][C:10]1([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[N:12]([CH2:20][CH3:21])[C:11]1=[O:22])(=O)C1C=CC=CC=1.O.[OH-].[K+].C(O)(=O)C>CO>[CH2:20]([N:12]1[C:13]2[C:18](=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:10]([OH:9])([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=2)[C:11]1=[O:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 863006811-Ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoate

Produkt 1

HCID 863005421-Ethyl-3-hydroxy-5-methyl-3-(3,4,5-trimethoxybenzyl)indolin-2-oneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Alternative route: To an oven dried Biotage microwave vial cooled under argon was added 1-ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoate (0.053 grams, 0.11 mmol). This was taken up in 0.6 mL of methanol, 0.6 mL of deionized water. A solution of KOH (223 μl, 2.0M in water) was added and the sealed vial was placed in the microwave and heated to 130° C. for 12 minutes, and 18 minutes at 140° C. Upon cooling the solution was neutralized with a stoichiometric amount of glacial acetic acid (Fisher scientific), and concentrated. Purification on a Teledyne ISCO using a C18 reverse phase column (water with 0.1% formic acid/acetonitrile gradient) afforded the desired compound. 85% yield. 1H NMR 7.22 (s, 1H), 7.08 (d, 1H), 6.55 (d, 1H), 6.06 (s, 2H), 4.38 (bs, OH), 3.72 (s, 3H), 3.66 (m, 1H), 3.61 (s, 6H), 3.34 (m, 1H), 3.23 (d, 1H), 3.17 (d, 1H), 2.35 (s, 3H), 0.87 (t, 3H). Calculated mass for C21H25NO5, 371.43. Observed 394.1 (M+Na)

Aufarbeitung

  1. customAlternative route: To an oven dried Biotage microwave
  2. temperaturevial cooled under argon
  3. custom18 minutes
  4. customat 140° C
  5. temperatureUpon cooling the solution
  6. concentrationconcentrated
  7. customPurification on a Teledyne ISCO

Quellen und Nachweise

ORD-Eintrag
ord-c3702aa8d9ad47ac9c0e43d109ceb312
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079853B2

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