Stannous chloride dihydrate → 2-Amino-4-(benzyloxy)-5-methoxybenzoic acid

HRID 432013

Reaction equation

HRID 432013 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([N+:20]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl>CO>[NH2:20][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]([O:18][CH3:19])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 108596334-(Benzyloxy)-5-methoxy-2-nitrobenzoic acid

Product 1

HCID 109676752-Amino-4-(benzyloxy)-5-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-benzyloxy-5-methoxy 2-nitrobenzoic acid (18.18 g, 60 mmol)(D. E. Thurston et al., Synthesis (1990), 81) and SnCl2.2H2O (137 g, 0.6 mol) (Showa Chemical Company, Japan) in MeOH (800 mL) was stirred at 70° C. for 5 h. The mixture was concentrated under vacuum to a thick syrup. Ethyl acetate (300 mL) was then added. The organic phase was washed with water until it turned to a clear solution, then washed with brine, and dried over MgSO4. After removal of solvent, the crude was recrystallized from ethyl acetate to obtain the title compound in the form of a yellow solid with a yield of 15.1 g (92%).

Workup

  1. concentrationThe mixture was concentrated under vacuum to a thick syrup
  2. additionEthyl acetate (300 mL) was then added
  3. washThe organic phase was washed with water until it
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removal of solvent
  7. customthe crude was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-87f565170a074cf9858bf3687fb98661
Source dataset
uspto-grants-2003_12
Patent number
US06660856B2

Linked notes

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