Stannous chloride dihydrate → Methyl 3-Amino-4-chlorobenzoate

HRID 538600Notes

Reaction equation

HRID 538600 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1.O.O.Cl[Sn]Cl>C(O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([NH2:11])[CH:5]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 593055Methyl 3-Amino-4-chlorobenzoateYield 69.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-Chloro-3-nitro-benzoic acid methyl ester (5.0 g, 23.19 mmol) in 100 ml of ethanol was added SnCl2.2H2O (26.0 g, 115.96 mmol) and the reaction mixture was heated at 80° C. for 2 h. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure. Water (100 mL) was added, basified the reaction mixture with NaOH solution and extracted with hot EtOAc (3×250 mL). The combined organics was dried over Na2SO4, filtered and concentrated to give the desired product (3.0 g, 69%).

Workup

  1. customAfter the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure
  2. additionWater (100 mL) was added
  3. extractionextracted with hot EtOAc (3×250 mL)
  4. dry with materialThe combined organics was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ee25f359e3d4428985e81c478cd33cbe
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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