4-Aminobenzoic Acid → HCID 2859933, compound

HRID 1870471Notes

Reaction equation

HRID 1870471 reaction equation
C([O-])([O-])=O.[K+].[K+].[NH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1.[CH:17]12[CH2:24][CH2:23][CH:20]([CH:21]=[CH:22]1)[CH:19]1[C:25]([O:27][C:28](=O)[CH:18]21)=[O:26]>O>[C:12]([C:11]1[CH:15]=[CH:16][C:8]([N:7]2[C:25](=[O:26])[CH:19]3[CH:18]([CH:17]4[CH2:24][CH2:23][CH:20]3[CH:21]=[CH:22]4)[C:28]2=[O:27])=[CH:9][CH:10]=1)([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 11430Potassium CarbonateHCID 220977Bicyclo(2.2.2)oct-5-ene-2,3-dicarboxylic Anhydride

Product 1

HCID 2859933HCID 2859933, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of K2CO3 (5.88 g, 42.5 mmol) in H2O (100 mL) was added 4-aminobenzoic acid (5.83 g, 42.5 mmol) and bicyclo[2.2.2]oct-5-en-2,3-dicarboxylic anhydride (7.20 g, 40.4 mmol). The reaction mixture was stirred at room temperature for 18 hrs. and then washed with ethylacetate (EtOAc) (75 ml,). The aqueous phase was acidified with conc. HCl until the pH reached 1. The precipitated crystals were filtered and dried: 11.77 g (98%), mp=269° C.

Workup

  1. washand then washed with ethylacetate (EtOAc) (75 ml,)
  2. filtrationThe precipitated crystals were filtered
  3. customdried

Sources & evidence

ORD record
ord-d11202a708e54d60b246f0915a507e11
Source dataset
uspto-grants-2000_08
Patent number
US06096811

Reaction notes

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