Hydrochloric Acid → diethyl 4-aminobenzene-1,2-dicarboxylate

HRID 2184629Notes

Reaction equation

HRID 2184629 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[CH:13][CH:14]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])([O-])=O.Cl.O.[OH-].[Na+]>C1C=CC=CC=1.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[CH:13][CH:14]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 263041diethyl 4-nitrophthalate

Product 1

HCID 237992diethyl 4-aminobenzene-1,2-dicarboxylateYield 82.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 241BenzeneSolvent

Procedure

Compound 401 (1.5 g, 5.6 mmol) was dissolved in 280 ml of benzene, and 3.4 g of purified zinc dust was added. Then 10 ml of concentrated hydrochloric acid was added in portions. After 15 min. of stirring at room temperature, another 3.4 g of zinc dust was added and the mixture was stirred at room temperature for 12 hours. 340 ml of cold water was added to the reaction mixture and the mixture was neutralized with 1N NaOH solution. The mixture was transferred to a separatory funnel and the benzene layer was removed. The aqueous layer was extracted with benzene. The combined benzene extracts were washed with water and dried over anhydrous sodium sulfate. After evaporation of the solvent, the pale yellow crude solid was obtained and purified by silica gel column chromatography (n-hexane: acetic acid =8:1) to give 1.1 g (80.6%) of diethyl 4-aminophthalate (compound 402).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. customThe mixture was transferred to a separatory funnel
  3. customthe benzene layer was removed
  4. extractionThe aqueous layer was extracted with benzene
  5. washThe combined benzene extracts were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter evaporation of the solvent
  8. customthe pale yellow crude solid was obtained
  9. custompurified by silica gel column chromatography (n-hexane: acetic acid =8:1)

Sources & evidence

ORD record
ord-85fe639a6f5c4eb49b5a9cfc36512e28
Source dataset
uspto-grants-2002_06
Patent number
US06399318B1

Reaction notes

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