3-Hydroxyanthranilic Acid → HCID 66620475, compound

HRID 415179Notes

Reaction equation

HRID 415179 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].N1C=CC=CC=1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25])([O-:20])=[O:19]>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:3]([NH:11][C:24]([C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)=[O:25])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 863-Hydroxyanthranilic AcidHCID 1049PyridineHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 66620475HCID 66620475, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (25 mL) was added to 3-nitrobenzoic acid (3 g, 18 mmol) and the mixture was stirred at reflux for 6 hr. Thionyl chloride was evaporated under reduced pressure and the residues was dried to obtain 3-nitrobenzoyl chloride as a yellow solid. 3-Hydroxyanthranilic acid (0.92 g, 6.0 mmol) and pyridine (1.45 mL, 18.0 mmol) were added to toluene (30 mL) and the mixture was stirred at room temperature for 30 min. Then 3-nitrobenzoyl chloride prepared above (3.34 g, 18 mmol) was added. The mixture was stirred at room temperature for 30 min and then at 80° C. for 2 hr. The solvents was evaporated under reduced pressure and the residue was washed with 5% aqueous hydrochloric acid (100 mL×3), filtered, the solid was washed with water (100 mL×3), dried in vacuum at 50° C. to obtain 3-hydroxy-2-(3-nitrobenzeneamido)benzoic acid as a yellow solid (1.8 g, yield 100%). LC-MS (ESI) m/z 303 [M+1]+.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. waitat 80° C. for 2 hr
  4. customThe solvents was evaporated under reduced pressure
  5. washthe residue was washed with 5% aqueous hydrochloric acid (100 mL×3)
  6. filtrationfiltered
  7. washthe solid was washed with water (100 mL×3)
  8. customdried in vacuum at 50° C.

Sources & evidence

ORD record
ord-94f1a6b010464dfeb258d1b6a50557dc
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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