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

HRID 1594513ノート

反応式

HRID 1594513 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aab7b33c4b0642408d941e85d8aa61ab
出典データセット
uspto-grants-2007_11
特許番号
US07301036B2

反応ノート

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