Water → 2-Amino-4,5-dichlorobenzoic acid

HRID 2265170Notes

Reaction equation

HRID 2265170 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O.[Li+].[OH-]>C1COCC1>[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 11694243Methyl 2-amino-4,5-dichlorobenzoate

Product 1

HCID 121045502-Amino-4,5-dichlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-amino-4,5-dichlorobenzoate (2.1 g, 9.41 mmol) was dissolved in THF (15 mL) and water (30 mL) was added. LiOH (0.79 g, 18.8 mmol) was added the mixture was stirred overnight at rt. The product was precipitated by addition of 10% aq. HCl (30 mL) and isolated by suction filtration. The white solid was dried under vacuum (1.6 g, 81%). 1H NMR (400 MHz, DMSO-d6): 7.78 (s, 1H), 7.01 (s, 1H).

Workup

  1. customThe product was precipitated by addition of 10% aq. HCl (30 mL)
  2. customisolated by suction filtration
  3. customThe white solid was dried under vacuum (1.6 g, 81%)

Sources & evidence

ORD record
ord-53b126169da841e7a3a20b968616c29c
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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