Ammonium Chloride → Methyl 3-amino-2-chlorobenzoate

HRID 1481311Notes

Reaction equation

HRID 1481311 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl-].[NH4+]>CO.[Zn]>[NH2:12][C:11]1[C:2]([Cl:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Product 1

HCID 15132848Methyl 3-amino-2-chlorobenzoateYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To the solution of 213A: (1 g, 4.64 mmol) in MeOH (23.19 ml) was added ammonium chloride (2.481 g, 4.64 mmol) and zinc dust (1.516 g, 23.19 mmol). The reaction was stirred at rt for 2 h, then warmed to 60° C. for 1 h. The reaction was filtered through a pad of Celite, rinsing with MeOH. The filtrate was concentrated. The residue was partitioned between EtOAc and water and the layers were separated. The organic layer washed with sat. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. Purification by silica gel chromatography afforded 213B (0.85 g, 99% yield) as a yellow oil. MS (ESI) m/z: 186.0 (M+H)+.

Workup

  1. temperaturewarmed to 60° C. for 1 h
  2. filtrationThe reaction was filtered through a pad of Celite
  3. washrinsing with MeOH
  4. concentrationThe filtrate was concentrated
  5. customThe residue was partitioned between EtOAc and water
  6. customthe layers were separated
  7. washThe organic layer washed with sat. NaHCO3, brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-48b7c8e950594411bdef001a36a92e8c
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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