2-Methyl-5-Nitroaniline → N-(5-Amino-2-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide

HRID 1805088

Reaktionsgleichung

Reaktionsgleichung von HRID 1805088
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:48][C:49]1[CH:54]=[CH:53][C:52]([N+:55]([O-])=O)=[CH:51][C:50]=1[NH2:58].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:55][C:52]1[CH:53]=[CH:54][C:49]([CH3:48])=[C:50]([NH:58][C:12]([C:3]2[C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][CH:4]=2)=[O:14])[CH:51]=1

Komponenten

8

Edukt 6

HCID 74442-Methyl-5-NitroanilineHCID 61436Stannous chloride dihydrateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524710HCID 178524710, Verbindung

Produkt 1

HCID 57567293N-(5-Amino-2-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamideAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 4-hydroxy-quinoline-3-carboxylic acid (A-1) (50 mg, 0.26 mmol), HBTU (99 mg, 0.26 mmol) and DIEA (138 μL, 0.79 mmol) in THF (2.6 mL) was added 2-methyl-5-nitro-phenylamine (40 mg, 0.26 mmol). The mixture was heated at 150° C. in the microwave for 20 min and the resulting solution was concentrated. The residue was dissolved in EtOH (2 mL) and SnCl2.2H2O (293 mg, 1.3 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was basified with sat. NaHCO3 solution to pH 7-8 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was dissolved in DMSO and purified by HPLC (10-99% CH3CN/H2O) to yield the product, N-(5-amino-2-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (94) (6 mg, 8%). HPLC ret. time 2.06 min, 10-99% CH3CN, 5 min run; ESI-MS 294.2 m/z (MH+).

Aufarbeitung

  1. concentrationthe resulting solution was concentrated
  2. dissolutionThe residue was dissolved in EtOH (2 mL)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in DMSO
  9. custompurified by HPLC (10-99% CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-ca94140c8d69416aaa80db601a5d2c1b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354427B2

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