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

HRID 1915431

반응식

HRID 1915431 반응식
[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

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
150 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-00383c1e5fc34d05b888d60d43a481fd
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614327B2

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