Hydrochloric Acid → 2-Amino-5-chloro-4-nitrobenzoic acid

HRID 2405756Notes

Reaction equation

HRID 2405756 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[C:5](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([Cl:11])[CH:10]=1)[NH2:6].[Li+].[OH-].Cl>C1COCC1.O>[Cl:11][C:9]1[CH:10]=[C:4]([C:3]([OH:15])=[O:2])[C:5]([NH2:6])=[CH:7][C:8]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 20327955HCID 20327955, compound

Product 1

HCID 214739642-Amino-5-chloro-4-nitrobenzoic acidYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-4-nitroanthranilic acid methyl ester (10.0 g, 43 mmol) in THF (120 mL) was added LiOH (2.7 g, 65 mmol) dissolved in water (40 mL). The reaction mixture was stirred at room temperature for 18 h and acidified to pH 4 with 1 N HCl. The aqueous layer was extracted with EtOAc (2×150 mL); the combined organic layers were dried over Na2SO4, filtered, and concentrated to give 5-chloro-4-nitroanthranilic acid (8.7 g, 88%) as an orange solid.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (2×150 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-98c9499e795d4462a949d9e089f8be16
Source dataset
uspto-grants-2014_08
Patent number
US08809326B2

Reaction notes

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