Hydrochloric Acid → 4-Amino-2-(methoxycarbonyl)-3-methyl-5-nitrobenzoic acid

HRID 561905Notes

Reaction equation

HRID 561905 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[C:5](=[C:10]([CH3:18])[C:11]([NH2:17])=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[OH-].[Na+].Cl>C1COCC1.O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[C:4](=[CH:13][C:12]([N+:14]([O-:16])=[O:15])=[C:11]([NH2:17])[C:10]=1[CH3:18])[C:3]([OH:19])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 597617814-Amino-3-methyl-5-nitro-phthalic acid dimethyl ester

Product 1

HCID 597616804-Amino-2-(methoxycarbonyl)-3-methyl-5-nitrobenzoic acidYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Amino-3-methyl-5-nitro-phthalic acid dimethyl ester (1.8 g, 6.72 mmol) in THF (10 mL) and water (20 mL) was added 5 N NaOH (4.0 mL) and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was acidified with conc. HCl (pH=2.0) and extracted with EtOAc (2×100 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo to afford the 4-Amino-3-methyl-5-nitro-phthalic acid 2-methyl ester (1.3 g, 76%) as a yellow solid.

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c60ff6b6f6744e49aa494fae7f67c69b
Source dataset
uspto-grants-2011_11
Patent number
US08063225B2

Reaction notes

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