Sulfuric Acid → Methyl 3-amino-5-chloro-2-nitrobenzoate

HRID 85137Notes

Reaction equation

HRID 85137 reaction equation
OS(O)(=O)=O.[NH2:6][C:7]1[C:8]([N+:17]([O-:19])=[O:18])=[C:9]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:10]([OH:12])=[O:11].[C:20]([O-])([O-])=O.[Na+].[Na+]>CO>[NH2:6][C:7]1[C:8]([N+:17]([O-:19])=[O:18])=[C:9]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:10]([O:12][CH3:20])=[O:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 107274793-Amino-5-chloro-2-nitrobenzoic acid

Product 1

HCID 12165619Methyl 3-amino-5-chloro-2-nitrobenzoateYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated H2SO4 (1.5 ml) was added to a mixture of 3-amino-5-chloro-2-nitrobenzoic acid (70; 3.5 g, 16.2 mmol) in MeOH (120 ml). The resulting reaction mixture was stirred under reflux for 3 days. It was then neutralized with saturated aqueous Na2CO3 and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography afforded methyl 3-amino-5-chloro-2-nitrobenzoate 71 (3.3 g, 88.5%) as a yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureunder reflux for 3 days
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-8de8b8d85a0e4346874e0359de4f6801
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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