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

HRID 1594513Notes

Reaction equation

HRID 1594513 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-aab7b33c4b0642408d941e85d8aa61ab
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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