Acetic Acid → 5-bromo-2-(ethoxycarbonyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid

HRID 523248

Reaktionsgleichung

Reaktionsgleichung von HRID 523248
Cl.[Br:2][C:3]1[C:11]([CH3:12])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([NH:13]N)[CH:4]=1.O=[C:16]1[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17]1.C(O)(=O)C>C1(C)C=CC=CC=1>[Br:2][C:3]1[C:11]([CH3:12])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]2[C:4]=1[C:21]1[CH2:20][CH2:19][CH:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][C:16]=1[NH:13]2

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 118096Ethyl 3-oxocyclohexanecarboxylateHCID 1177610194-Bromo-2-hydrazinyl-5-methylbenzoic acid hydrochloride

Produkt 1

HCID 1177754535-bromo-2-(ethoxycarbonyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acidAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
117 °C

Versuchsvorschrift

A mixture of 4-bromo-2-hydrazinyl-5-methylbenzoic acid hydrochloride (2.17 g, 7.71 mmol), ethyl 3-oxocyclohexanecarboxylate (1.44 g, 8.48 mmol) and acetic acid (1.32 mL, 23.1 mmol) in toluene (40 mL) was heated in an oil bath at 117° C. for 5 h. The mixture was concentrated and dried under vacuum, and the residue was diluted with toluene (18 mL) and TFA (4.5 mL). The mixture was heated at 90° C. overnight. The cooled mixture was diluted with EtOAc, sonicated, and the precipitate was collected by filtration and washed with EtOAc to give a yellow solid. The filtrate was concentrated and the residue was suspended in EtOAc with sonication. The precipitate was collected by filtration and combined with the first precipitate. The solid was triturated with MeOH to give 5-bromo-2-(ethoxycarbonyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid as a pale yellow solid (1.60 g, 55% yield). Mass spectrum m/z 380, 382 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customdried under vacuum
  3. additionthe residue was diluted with toluene (18 mL) and TFA (4.5 mL)
  4. temperatureThe mixture was heated at 90° C. overnight
  5. additionThe cooled mixture was diluted with EtOAc
  6. customsonicated
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with EtOAc
  9. customto give a yellow solid
  10. concentrationThe filtrate was concentrated
  11. customthe residue was suspended in EtOAc with sonication
  12. filtrationThe precipitate was collected by filtration
  13. customThe solid was triturated with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-3757c9ebbabb4d82bc41aa9394744026
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334290B2

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