Methyl 4-oxocyclohexanecarboxylate → methyl 6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

HRID 527452

Reaktionsgleichung

Reaktionsgleichung von HRID 527452
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.O=[C:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1>C(O)(=O)C.O>[CH3:2][O:3][C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:10][C:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][C:14]2=1

Komponenten

5

Edukt 2

HCID 226643Methyl 4-oxocyclohexanecarboxylateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Produkt 1

HCID 84612962methyl 6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(4-Methoxyphenyl)hydrazine hydrochloride (80.0 mg, 0.46 mmol) and methyl 4-oxocyclohexanecarboxylate (85.9 mg, 0.55 mmol) were dissolved in acetic acid (0.5 mL). The mixture was heated at 80° C. with stirring under nitrogen for 3 h, cooled, diluted with water (2 mL) and the resulting precipitate was collected by filtration, gently washed with water and dried in vacuo to yield the title compound (107 mg, 90%) as an off-white solid. C15H17NO3, Mr=259.30; 1H NMR (400 MHz, DMSO-d6) d: 1.81-1.91 (m, 1H), 2.15-2.19 (m, 1H), 2.66-2.84 (m, 4H), 2.90 (dd, J=4.6/14.2 Hz, 1H), 3.65 (s, 3H), 3.72 (s, 3H), 6.61 (dd, J=2.4/8.8 Hz, 1H), 6.86 (d, J=2.4 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 10.51 (s, 1H); LCMS (ESI) tR: 2.27 min (>99%, ELSD), m/z: 260.2 [M+1]+.

Aufarbeitung

  1. temperaturecooled
  2. filtrationthe resulting precipitate was collected by filtration
  3. washgently washed with water
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a35267a0f38e4b21b9f2e2a980163304
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346803B2

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