Stannous chloride dihydrate → methyl 2-[({2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-aminobenzoate

HRID 41800Notes

Reaction equation

HRID 41800 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:27]3[C:36]([N+:37]([O-])=O)=[CH:35][CH:34]=[CH:33][C:28]=3[C:29]([O:31][CH3:32])=[O:30])=[CH:21][CH:20]=2)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>CO>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:27]3[C:36]([NH2:37])=[CH:35][CH:34]=[CH:33][C:28]=3[C:29]([O:31][CH3:32])=[O:30])=[CH:21][CH:20]=2)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69916720methyl 2-[({2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate2×

Product 1

HCID 69916718methyl 2-[({2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-aminobenzoateYield 84.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-[({2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate (compound 21b, 8.396 g) and tin (II) chloride dihydrate (13.56 g) in methanol (155 mL) was heated under reflux for 2 hr. The reaction mixture was concentrated under reduced pressure, and to the concentrated residue were added saturated aqueous sodium hydrogen carbonate and ethyl acetate. The mixture was stirred for 1 hr, and filtered, and the insoluble material was washed with ethyl acetate. The filtrate and washing were combined, and concentrated under reduced pressure, and the concentrated solution was extracted with ethyl acetate. The ethyl acetate solution of the resultant product was dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the concentrated residue was purified by silica gel column (hexane→thexane:AcOEt=5:1→4:1→3:1→2:1→3:2) to give methyl 2-[({2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-aminobenzoate (compound 22b) (6.68 g, 84%) as a brown amorphous solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionto the concentrated residue were added saturated aqueous sodium hydrogen carbonate and ethyl acetate
  5. filtrationfiltered
  6. washthe insoluble material was washed with ethyl acetate
  7. washThe filtrate and washing
  8. concentrationconcentrated under reduced pressure
  9. extractionthe concentrated solution was extracted with ethyl acetate
  10. dry with materialThe ethyl acetate solution of the resultant product was dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. customthe concentrated residue was purified by silica gel column (hexane→thexane:AcOEt=5:1→4:1→3:1→2:1→3:2)

Sources & evidence

ORD record
ord-6d2143a7f10a4486995a19065cda3944
Source dataset
uspto-grants-2013_09
Patent number
US08530506B2

Reaction notes

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