Methyl 2-chloro-5-nitrobenzoate → Methyl 5-Amino-2-chlorobenzoate

HRID 1507640Notes

Reaction equation

HRID 1507640 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[Cl:13]>C(O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[Cl:13]

Participants

3

Reactant 1

HCID 22754Methyl 2-chloro-5-nitrobenzoate

Product 1

HCID 5200412Methyl 5-Amino-2-chlorobenzoateYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-5-nitro-benzoic acid methyl ester 15 (4.3 g, 20.2 mmol), SnCl2-2H2O (45.5 g, 201.8 mmol) and ethanol (100 mL) were combined into a sealed pressure vial and was sonicated for 2 hr. The solvent was concentrated and the residue was dissolved in EtOAc, washed with NaHCO3, brine, dried over MgSO4 and filtered. The solvent was evaporated to give the desired product 16 (2.8 g, 73%).

Workup

  1. customwas sonicated for 2 hr
  2. concentrationThe solvent was concentrated
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9f983ed95b7d40b99863e7ae45aaed8d
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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