4-Nitroanthranilic acid → 4-Nitro-isatoic anhydride

HRID 1175788Notes

Reaction equation

HRID 1175788 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-:3])=[O:2].Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[C:8](=[O:10])[O:9][C:15](=[O:17])[NH:13][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 120764-Nitroanthranilic acidHCID 94429Triphosgene

Product 1

HCID 2820894-Nitro-isatoic anhydrideYield 20,285.801%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 4-nitroanthranilic acid (9.11 g), triphosgene (4.92 g) and tetrahydrofuran (240 ml) was stirred for 10 hours at 45° C. The precipitated solids were collected by filtration, washed with tetrahydrofuran, and then dried to obtain the target product (700 g).

Workup

  1. filtrationThe precipitated solids were collected by filtration
  2. washwashed with tetrahydrofuran
  3. customdried

Sources & evidence

ORD record
ord-02042def898647ecb57e7d9c13f875cd
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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