Ammonium Chloride → 3-Amino-2,6-dichlorobenzoic acid

HRID 1943857Notes

Reaction equation

HRID 1943857 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]([Cl:14])[C:3]=1[C:4]([OH:6])=[O:5].[NH4+].[Cl-]>C1COCC1.[Zn]>[NH2:11][C:10]1[C:2]([Cl:1])=[C:3]([C:7]([Cl:14])=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 5213073-Amino-2,6-dichlorobenzoic acidYield 75.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2,6-Dichloro-3-nitrobenzoic acid (2.13 g, 9.03 mmol) was dissolved in 2:1 THF:saturated aqueous NH4Cl and cooled to 0° C. The mixture was treated with zinc (11.8 g, 181 mmol). The reaction mixture was allowed to warm to ambient temperature and stir for 24 hours. The reaction mixture was filtered through GF/F paper while rinsing with THF. The mixture was acidified to a pH of 1 using 1.0M HCl and extracted with 15% 2-propanol:DCM (3×). The extracts were washed with water and brine, dried over sodium sulfate and concentrated to afford 3-amino-2,6-dichlorobenzoic acid (1.40 g, 6.82 mmol, 75.5% yield). MS (APCI-neg) m/z=203.6 (M−H).

Workup

  1. filtrationThe reaction mixture was filtered through GF/F paper
  2. washwhile rinsing with THF
  3. extractionextracted with 15% 2-propanol
  4. washThe extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c283bfd695d44ffa6afa3a709ca443d
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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