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Hydrochloric Acid → 8-(2-Chlorophenyl)-6-methyl-1,8-dihydropyrido [2,1-c][1,4]-oxazine-7,9-dicarboxylic acid 9-ethyl 7-methyl ester

HRID 1253
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1253
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:8]([CH2:12][O:13][CH2:14][CH:15](OC)OC)[NH:9][C:10]=1[CH3:11])=[O:4].Cl>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:8]2[N:9]([C:10]=1[CH3:11])[CH:15]=[CH:14][O:13][CH2:12]2)=[O:4]
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 698306344-(2-Chlorophenyl)-2-(2,2-dimethoxy-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

Produkt 1

HCID 867521818-(2-Chlorophenyl)-6-methyl-1,8-dihydropyrido [2,1-c][1,4]-oxazine-7,9-dicarboxylic acid 9-ethyl 7-methyl esterAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-chlorophenyl)-2-(2,2-dimethoxy-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (XX, 9.2 g) in tetrahydrofuran (200 mL) was added 3N hydrochloric acid (40 mL). The mixture was then refluxed for 4 h. On cooling to room temperature, tetrahydrofuran was removed under reduced pressure and the residue taken up in ethyl acetate (200 mL). The organic phase was washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å) using a solvent mixture of hexane and ethyl acetate as eluent (90:10; 1L) as eluent to afford the title compound (XXI 5.2 g). 1H-NMR (CDCl3) δ (ppm): 1.22 (t, 3H, J=7.1 Hz), 2.43 (s, 3H), 3.68 (s, 3H), 4.12 (q, 2H, J=7. 1 Hz),4,60(d,1H, J=13.5 Hz), 5.48 (s, 1H), 5.70 (d, 1H, J=13.8 Hz), 6.21 (d, 1H, J=4.7 Hz), 6.30(d, 1H, J=4.6 Hz), 7.07-7.28 (m, 4H); 13C-NMR (CDCl3) δ (ppm): 14.1, 15.7, 36.6, 51.2, 60.6, 63.5, 105.8, 106.7, 107.8, 127.3, 127.8, 129.5, 130.4, 131.8, 132.5 139.2, 142.0, 143.4, 166.4, 168.1; HRMS: calc. for C20H20CIN2O5 389.1030 found 389.1020; Elemental Analysis (%): calc. (found) C 61.62 (61.78), H 5.17 (5.27), N 3.59 (3.51); M.p. 126.0°-126.8° C.; IR (KBr, cm-1): 1693, 1662, 1645, 1581.

Aufarbeitung

  1. temperatureThe mixture was then refluxed for 4 h
  2. customtetrahydrofuran was removed under reduced pressure
  3. washThe organic phase was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å)
  8. additiona solvent mixture of hexane and ethyl acetate as eluent (90:10; 1L) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1b853575abe94e7c8c35c82d1e1ed7b0
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05723618

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