Phosphorus oxychloride → 1-Chloro-4-hydroxy-7-iodo-isoquinoline-3-carboxylic acid butyl ester

HRID 1618237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618237
[CH2:1]([O:5][C:6]([C:8]1[NH:9][C:10](=O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([I:19])[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].O=P(Cl)(Cl)[Cl:23]>>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Cl:23])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([I:19])[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 667132364-Hydroxy-7-iodo-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester

Produkt 1

HCID 860145321-Chloro-4-hydroxy-7-iodo-isoquinoline-3-carboxylic acid butyl ester

Versuchsvorschrift

0.215 g of 4-hydroxy-7-iodo-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester were added to 5 ml of POCl3 at room temperature. The mixture was refluxed for 3 h and POCl3 was removed under vacuum. The residue was dissolved in ethyl acetate and the solution was washed with satd. aqueous sodium bicarbonate, dried (MgSO4), filtered, and concentrated to give 0.205 g of a while solid: Proton NMR (200 MHz, chloroform-d) δ 11.91 (s, 1H), 8.67 (m, 1H), 8.10 (m, 2H), 4.49 (t, J=7 Hz, 2H), 1.95-1.75 (m, 2H), 1.60-1.39 (m, 2H), 1.00 (t, J=7 Hz, 3H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h
  2. customPOCl3 was removed under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with satd
  5. dry with materialaqueous sodium bicarbonate, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 0.205 g of a while solid

Quellen und Nachweise

ORD-Eintrag
ord-040190a229894c3c8b1c540ca4972944
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765956B2

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