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

HRID 2184631Notes

Reaction equation

HRID 2184631 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])[C:7](=[CH:15][CH:16]=1)[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])([O-])=O.Cl.O.[OH-].[Na+]>C1C=CC=CC=1.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])[C:7](=[CH:15][CH:16]=1)[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22457397HCID 22457397, compound

Product 1

HCID 22457404Dibutyl 4-aminobenzene-1,2-dicarboxylateYield 89.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 241BenzeneSolvent

Procedure

Compound 403 (1.5 g, 4.6 mmol) was dissolved in 230 ml of benzene and then 2.8 g of purified zinc dust was added. Concentrated hydrochloric acid (8.2 ml) was added in portions. After 15 minutes of stirring at room temperature, another 2.8 g of zinc dust was added and the mixture was stirred at room temperature for 12 hours. Then 280 ml of 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 residue was purified by silica gel column chromatography (n-hexane: acetic acid =10:1) to give 980 mg (89.6%) of di-n-butyl 4-aminophthalate (compound 404).

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 residue was purified by silica gel column chromatography (n-hexane: acetic acid =10:1)

Sources & evidence

ORD record
ord-12570378c8774ebe964422d466b37db5
Source dataset
uspto-grants-2002_06
Patent number
US06399318B1

Reaction notes

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