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

HRID 74103

反応式

HRID 74103 の反応式
[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

参加物

8

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-93b084af9c8b4076b9ce5a1f26dc07d4
出典データセット
uspto-grants-2014_09
特許番号
US08829204B2

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