2-Amino-5-nitrobenzoic acid → 5-Nitro-2-(pyrrol-1-yl)benzoic acid

HRID 2227468Notes

Reaction equation

HRID 2227468 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1>C(O)(=O)C>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]([N:1]2[CH:16]=[CH:20][CH:19]=[CH:18]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 120322-Amino-5-nitrobenzoic acidHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 121962005-Nitro-2-(pyrrol-1-yl)benzoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-5-nitrobenzoic acid (475 mg), 2,5-dimethoxytetrahydrofuran (345 mg) and acetic acid (10 ml) was heated under reflux for 3 hours and then concentrated at reduced pressure. Brine was added to the resulting residue and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1) to give the titled compound (yield, 73%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated at reduced pressure
  4. additionBrine was added to the resulting residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-70e317d51d3048dab986c281029323ce
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

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