Stannous Chloride → 2-Methoxycarbonylmethyl-5-amino-benzoic acid methyl ester

HRID 869422Notes

Reaction equation

HRID 869422 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15].Cl[Sn]Cl>CO>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 123467632-Methoxycarbonylmethyl-5-nitro-benzoic acid methyl ester

Product 1

HCID 123467642-Methoxycarbonylmethyl-5-amino-benzoic acid methyl esterYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

2-methoxycarbonylmethyl-5-nitro-benzoic acid methyl ester (2.2 g, 8.8 mmol) was dissolved in MeOH (30 mL), then heated to 50° C. To the solution was added SnCl2 (5.89 g, 31 mmol) in batches. The reaction mixture was stirred at this temperture for 1 day. TLC monitored the reaction. After the reaction completed, the solvent was evaporated. To the residue was added ethyl acetate and base, adjusted pH to 8˜9, then filtered though celite and washed with ethyl acetate. The organic layer of the filtrate was collected and washed with water, dried over anhydrous Na2SO4 and concentrated to give 1.3 g of 5-amino-2-methoxycarbonylmethyl-benzoic acid methyl ester (18D).

Workup

  1. customthe reaction
  2. customthe solvent was evaporated
  3. additionTo the residue was added ethyl acetate and base
  4. filtrationfiltered though celite
  5. washwashed with ethyl acetate
  6. customThe organic layer of the filtrate was collected
  7. washwashed with water
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-050ff54ec1a94c338a060bbf0c8ba0a2
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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