4-Nitroanthranilic acid → 4-Nitro-isatoic anhydride

HRID 1687583Notes

Reaction equation

HRID 1687583 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[N+:11]([C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[O:5][C:15](=[O:17])[NH:1][C:2]=2[CH:10]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 120764-Nitroanthranilic acidHCID 94429Triphosgene

Product 1

HCID 2820894-Nitro-isatoic anhydrideYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Amino-4-nitro-benzoic acid (1.00 g, 0.00549 mol) was dissolved in THF. Triphosgene (1.63 g, 0.00549 mol) was dissolved in THF and added. The reaction mixture was stirred at rt for 2 h, concentrated, triturated with H2O, filtered, and taken up in acetone to afford a pale yellow solid (1.14 g, 99.8%).

Workup

  1. additionadded
  2. concentrationconcentrated
  3. customtriturated with H2O
  4. filtrationfiltered

Sources & evidence

ORD record
ord-6b7d6ed0e9df48f193ae327d1ee67321
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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