3-[(1-Methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide → 3-hydroxy-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 1011682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011682
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([O:20]CC2C=CC=CC=2)[CH:19]=1)[C:8]([NH:10][C:11]1[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=1)=[O:9])[CH3:3]>CO>[OH:20][C:18]1[CH:17]=[C:7]([CH:6]=[C:5]([O:4][CH:2]([CH3:3])[CH3:1])[CH:19]=1)[C:8]([NH:10][C:11]1[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=1)=[O:9]

Komponenten

3

Edukt 1

HCID 536296253-[(1-Methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide

Produkt 1

HCID 591271833-hydroxy-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-[(1-Methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide (51 g; 0.14 mol) was dissolved in methanol (500 mL) and THF (500 mL) and the flask evacuated and purged with argon (3 times). 10% Palladium on carbon (5.1 g) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off through celite, and the filtrate concentrated in vacuo. Ethyl acetate was added and filtered to give the desired compound. (30.5 g). A second crop of material was obtained in the same way (4.0 g).

Aufarbeitung

  1. customTHF (500 mL) and the flask evacuated
  2. custompurged with argon (3 times)
  3. addition10% Palladium on carbon (5.1 g) was added
  4. customthe flask further evacuated
  5. customfinally purged with hydrogen gas
  6. customThe reaction mixture was evacuated
  7. custompurged with nitrogen (3 times)
  8. filtrationThe catalyst was filtered off through celite
  9. concentrationthe filtrate concentrated in vacuo
  10. additionEthyl acetate was added
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-a486ded2ae234222b13e05e4b9333652
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977328B2

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