2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → ethyl 1-(2-hydroxyethyl)-8-methoxy-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 45791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45791
[OH:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[C:13]([O:17][CH3:18])[N:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:5]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[OH:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[C:13]([O:17][CH3:18])[N:12]=[CH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:5]1

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67975686HCID 67975686, Verbindung

Produkt 1

HCID 67975382ethyl 1-(2-hydroxyethyl)-8-methoxy-1H-pyrazolo[4,3-h]quinazoline-3-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of ethyl 1-(2-hydroxyethyl)-8-methoxy-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate 1.2 g (3.76 mmol) in toluene (20 ml), 500 mg (2.2 mmol) 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile were added. The mixture was submitted to microwave irradiation at 100° for 3 hours in a sealed vial. The volatiles were evaporated, the crude was dissolved with ethyl acetate and portioned with sat. NaHCO3, the organic layer concentrated to dryness. The residue was purified by chromatography (ethyl acetate/hexane 7/3) to afford the desired compound 520 mg (46%). HRMS (ESI) calcd for C15H16N4O4 [M+H]+ 317.3119 found 317.3126.

Aufarbeitung

  1. additionwere added
  2. customirradiation at 100° for 3 hours in a sealed vial
  3. customThe volatiles were evaporated
  4. dissolutionthe crude was dissolved with ethyl acetate
  5. concentrationthe organic layer concentrated to dryness
  6. customThe residue was purified by chromatography (ethyl acetate/hexane 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-69672cf869ec4487bcf55f83dd5f4f2b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541576B2

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