3-Hydroxyanthranilic Acid → Methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate

HRID 969822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 969822
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.[CH3:22]CN(C(C)C)C(C)C.CI>CN(C=O)C.C(OCC)(=O)C.Cl>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]2[O:1][C:2]3[C:3](=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[CH:9][CH:10]=3)[N:11]=2)=[CH:15][CH:14]=1.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]2[O:18][C:2]3[C:3](=[C:4]([C:5]([O:7][CH3:22])=[O:6])[CH:8]=[CH:9][CH:10]=3)[N:11]=2)=[CH:15][CH:14]=1

Komponenten

9

Edukt 4

HCID 863-Hydroxyanthranilic AcidHCID 6328Methyl iodideHCID 85014-Chlorobenzoyl chlorideHCID 81531Diisopropylethylamine

Produkt 2

HCID 596258542-(4-Chlorophenyl)benzoxazole-4-carboxylic acidHCID 68459315Methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(4-Chlorophenyl)benzoxazole-4-carboxylic acid was prepared from 3-hydroxyanthranilic acid and 4-chlorobenzoyl chloride using the method described in Step A of Example 1. This crude material (2.90 g, 10.6 mmol) was directly dissolved in DMF (40 mL), DIPEA (5.46 g, 42.4 mmol) and methyl iodide (5.93 g, 42.4 mmol) added and the reaction stirred at room temperature for 18 h. After this time the reaction was diluted with ethyl acetate (100 mL) and 2 N HCl (50 mL). The organic layer was separated and then washed with 2 N HCl (25 mL), water (50 mL) and brine (50 mL). The organic layer was then dried over sodium sulfate, filtered and concentrated to dryness to yield light yellow oil. This material was purified using silica gel chromatography to afford 0.532 g (30% yield) of methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.28 (dd, J=6.9, 1.8 Hz, 2H), 8.04 (d, J=8.1 Hz, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.52 (d, J=8.7 Hz, 2H), 7.43 (t, J=7.8 Hz, 1H), 4.06 (s, 3H); MS (ESI) m/z 288 [M+H]+

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with 2 N HCl (25 mL), water (50 mL) and brine (50 mL)
  3. dry with materialThe organic layer was then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customto yield light yellow oil
  7. customThis material was purified

Quellen und Nachweise

ORD-Eintrag
ord-c9915bb799514e78a4f761b8686333f9
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07307094B2

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