Triethylamine → methyl5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline-10-carboxylate

HRID 1642343

Reaktionsgleichung

Reaktionsgleichung von HRID 1642343
Br[CH2:2][C:3]1[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C1(=O)O[C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]2[CH2:16]1.C(N(CC)CC)C>C(#N)C>[O:20]=[C:19]1[C:18]2[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]2[CH2:2][C:3]3[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[NH:14]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 12801Homophthalic anhydrideHCID 17837598Methyl 2-(bromomethyl)-3-cyanobenzoate

Produkt 1

HCID 58772535methyl5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline-10-carboxylateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A mixture of methyl 2-bromomethyl-3-cyanobenzoate (14.1 g, 55.5 mmol) and homophthalic anhydride (22.5 g, 138.8 mmol) in acetonitrile (150 mL) was stirred at room temperature. A solution of triethylamine (23.2 mL) in acetonitrile (100 mL) was added dropwise over the period of 1 hour. After the completion of addition, the resultant suspension was refluxed for 4 hours. The reaction mixture was then cooled to room temperature and filtered. The resultant solid was washed thoroughly with acetonitrile (100 mL) and ethanol (2×100 mL) and dried in vacuum oven at 50° C. to provide methyl 5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline-10-carboxylate was obtained in 81% yield (13.1 g). 1H NMR spectrum (in DMSO-d6): δ 12.21 (s, 1H); 8.20 (m, 2H); 7.83 (d, J=7.5 Hz, 1H); 7.71 (m, 2H); 7.47 (m, 2H); 4.07 (s, 2H); 3.89 (s, 3H).

Aufarbeitung

  1. additionAfter the completion of addition
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered
  4. washThe resultant solid was washed thoroughly with acetonitrile (100 mL) and ethanol (2×100 mL)
  5. customdried in vacuum oven at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-82260941896c4961bad159bfc6ae7c07
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119654B2

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