Hydrochloric Acid → 3-Amino-5-methoxy-[1,1'-biphenyl]-4-carboxamide

HRID 922391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922391
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[C:8]#[N:9].[OH-:18].[K+].Cl>CCO>[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[C:8]([NH2:9])=[O:18]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 867193553-Amino-5-methoxy-[1,1'-biphenyl]-4-carbonitrile

Produkt 1

HCID 867193563-Amino-5-methoxy-[1,1'-biphenyl]-4-carboxamideAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-amino-5-methoxy-[1,1′-biphenyl]-4-carbonitrile (4, 0.64 g, 2.86 mmol) and KOH (1.12 g, 20 mmol) in EtOH (24 mL) in a sealed tube was heated at 100° C. for 18 h. Additional KOH (0.56 g, 10 mmol) was added and heating was continued for another 18 h. After this time, the mixture was cooled to room temperature, and the pH was adjusted to ˜2 by addition of concentrated HCl. After concentration, the residue was partitioned between ethyl acetate (100 mL) and water (50 mL). The extracts were washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with methanol in dichloromethane (0-20%) to afford the title compound (0.28 g, 40%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.62-7.60 (m, 2H), 7.58 (s, 1H), 7.47-7.44 (m, 2H), 7.39-7.36 (m, 1H), 7.28 (s, 1H), 6.61 (d, J=1.5 Hz, 1H), 6.56 (s, 2H), 6.43 (d, J=1.5 Hz, 1H), 3.87 (s, 3H); ESI MS m/z 243 [M+H]+.

Aufarbeitung

  1. temperatureheating
  2. temperatureAfter this time, the mixture was cooled to room temperature
  3. concentrationAfter concentration
  4. customthe residue was partitioned between ethyl acetate (100 mL) and water (50 mL)
  5. washThe extracts were washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with methanol in dichloromethane (0-20%)

Quellen und Nachweise

ORD-Eintrag
ord-9c81eab7fcbd4bfa8f1dbf6683da426e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278940B2

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