Ammonium Chloride → 3-(4-Amino-2,6-dichloro-phenoxy)-quinoline-8-carboxylic acid methyl ester

HRID 1819771노트

반응식

HRID 1819771 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([N+:23]([O-])=O)=[CH:18][C:17]=1[Cl:26])=[CH:10]2)=[O:4].[NH4+].[Cl-]>CCO.C1COCC1.O.[Fe]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:16]1[C:17]([Cl:26])=[CH:18][C:19]([NH2:23])=[CH:20][C:21]=1[Cl:22])=[CH:10]2)=[O:4]

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 574409423-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester

생성물 1

HCID 574409393-(4-Amino-2,6-dichloro-phenoxy)-quinoline-8-carboxylic acid methyl ester수율 118.7%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 18504229Ethanol tetrahydrofuran water용매

실험 절차

To a solution of 3-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester (98) (1.26 mmol) and NH4Cl (370 mg, 6.91 mmol) in EtOH/THF/H2O=8 mL/4 mL/2 mL was added iron powder (386 mg, 6.91 mmol). The reaction mixture was refluxed for 3.5 h. After cooling to room temperature and insoluble materials were filtered by Celite filtration. The filtrate was concentrated and sat NaHCO3 was added to the residue, which was extracted twice with AcOEt. Organic layer was washed by brine, dried over MgSO4, and concentrated. Crude residue was purified by column chromatography (hexane/AcOEt=2/1, 80 g of silica gel) to afford compound 99 (543 mg). 1H NMR (300 MHz, DMSO-d6) δ 3.91 (3H, s), 5.77 (2H, br s), 6.78 (2H, s), 7.50 (1H, d, J=3.0 Hz), 7.61 (1H, dd, J=8.1 Hz), 7.81 (1H, dd, J=1.4, 6.4 Hz), 8.08 (1H, dd, J=1.4 Hz, 6.4 Hz), 8.93 (1H, d, J=3.0 Hz).

후처리

  1. temperatureThe reaction mixture was refluxed for 3.5 h
  2. filtrationinsoluble materials were filtered by Celite filtration
  3. concentrationThe filtrate was concentrated
  4. additionwas added to the residue, which
  5. extractionwas extracted twice with AcOEt
  6. washOrganic layer was washed by brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customCrude residue was purified by column chromatography (hexane/AcOEt=2/1, 80 g of silica gel)

출처 및 근거

ORD 기록
ord-5e4b46b0b6c54075add00c20df63a6f9
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601841B2

반응 노트

불러오는 중…