Hydrochloric Acid → Methyl 4-(4'-amino-3'-methoxy-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

HRID 2427338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2427338
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:27])[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.Cl>C(O)C.[Fe]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:27])[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:17]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 21985714Methyl 4-(3'-methoxy-4'-nitro-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

Produkt 1

HCID 21985857Methyl 4-(4'-amino-3'-methoxy-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(3′-methoxy-4′-nitro-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (670 mg, 1.80 mmol) in 85% aqueous ethanol (27 mL) was added iron powder (1.01 g, 18.04 mmol) and 2 N aqueous HCl (0.9 mL, 1.8 mmol), and the resulting suspension was heated at reflux for 2.5 h. The mixture was then cooled to rt, and filtered through a pad of Celite®. Water was added, the mixture was extracted with ethyl acetate, and the combined organic phases were dried over anhydrous sodium sulfate. Solvent was removed under reduced pressure and the residue was triturated with ethyl acetate/hexane to afford methyl 4-(4′-amino-3′-methoxy-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (410 mg, 67%). LC-MS ret. time 2.58 min, m/z 342.1 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.31 (s, 6H), 3.28 (s, 2H), 3.66 (s, 3H), 3.90 (s, 3H), 6.75 (d, 1H), 7.02-7.09 (m, 2H), 7.59 (d, 2H), 7.94 (d, 2H).

Aufarbeitung

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 2.5 h
  3. filtrationfiltered through a pad of Celite®
  4. additionWater was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialthe combined organic phases were dried over anhydrous sodium sulfate
  7. customSolvent was removed under reduced pressure
  8. customthe residue was triturated with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ffa997a020e7482e891bf2ab5e9effa6
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968576B2

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