Stannous chloride dihydrate → Methyl 4-{[(2-amino-4-chlorophenyl)amino]methyl}benzoate

HRID 1594513

반응식

HRID 1594513 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[C:4]([N+:20]([O-])=O)[CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:20][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 69417003Methyl 4-{[(4-chloro-2-nitrophenyl)amino]methyl}benzoate

생성물 1

HCID 68996953Methyl 4-{[(2-amino-4-chlorophenyl)amino]methyl}benzoate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

The title compound of Example 12, Step A (3.6 mmol, 1.2 g) and SnCl2.2H2O (18 mmol, 4 g) were heated in DMP (10 mL) at 40° C. for 3 hr. The reaction mixture was poured into EtOAc and concentrated NaHCO3 and stirred. The resulting mixture was filtered over celite, and the filter cake was washed with EtOAc. The organic phase was collected, dried with Na2SO4 and reduced in vacuo. Flash chromatography on silica eluting with 20% and 30% EtOAc in hexanes afforded the product as a pale white solid. 1H NMR (500 MHz, d6-DMSO) δ 7.94 (d, J=8.2 Hz, 2H), 7.49 (d, J=8.2 Hz, 2H), 6.70 (s, 1H), 6.32 (s, 1H), 5.68 (t, J=5.8 Hz, 1H), 5.07 (s, 2H), 4.41 (d, J=5.7 Hz, 2H), 3.85 (s, 3H). LC-MS (ESI, Method C) 3.33 min, 291.2 (M+1).

후처리

  1. filtrationThe resulting mixture was filtered over celite
  2. washthe filter cake was washed with EtOAc
  3. customThe organic phase was collected
  4. dry with materialdried with Na2SO4

출처 및 근거

ORD 기록
ord-aab7b33c4b0642408d941e85d8aa61ab
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07301036B2

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