Acetic Acid → HCID 68587091, Verbindung

HRID 17533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17533
[CH3:1][N:2]([CH3:25])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]#[N:21])=[C:10]([N+:22]([O-])=O)[CH:9]=2)[CH2:4]1.C(O)(=O)C.O.O.[Sn](Cl)Cl.[OH-].[Na+]>Cl.C(OCC)(=O)C.CO>[NH2:22][C:10]1[CH:9]=[C:8]([N:5]2[CH2:6][CH2:7][C@H:3]([N:2]([CH3:1])[CH3:25])[CH2:4]2)[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:12][C:11]=1[C:20]#[N:21]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 68586542HCID 68586542, Verbindung

Produkt 1

HCID 68587091HCID 68587091, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-4-nitrobiphenyl-3-carbonitrile (I-242) (7.9 g, 23.5 mmol) was dissolved in concentrated hydrochloric acid (40 ml), and at room temperature, acetic acid (4.0 ml, 70.5 mmol) and methanol (10 ml) were added, followed by cooling at 0° C., and tin(II) chloride dihydrate (15.9 g, 70.5 mmol) was gradually added. After stirred at the same temperature for 20 minutes, this was further stirred at room temperature for 20 minutes. At room temperature, methanol (30 ml) was added to the suspension, followed by stirring at the same temperature for 24 hours. The reaction liquid was fractionated with ethyl acetate and aqueous 1 M sodium hydroxide solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was subjected to column chromatography with silica gel, and the fraction with chloroform:methanol=95:5 gave the entitled compound (6.475 g, 90%) as a pale brown gel.

Aufarbeitung

  1. stirringthis was further stirred at room temperature for 20 minutes
  2. stirringby stirring at the same temperature for 24 hours
  3. customThe reaction liquid
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away

Quellen und Nachweise

ORD-Eintrag
ord-a40ef0f6b3394eb8975030275c29634e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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