4-Nitroanthranilic acid → HCID 13755419, compound

HRID 980034Notes

Reaction equation

HRID 980034 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].[C:14](Cl)(=[O:19])[CH2:15][C:16](Cl)=[O:17]>O1CCOCC1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:13][C:14](=[O:19])[CH2:15][C:16]([NH:13][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=[O:9])=[O:17])[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 120764-Nitroanthranilic acidHCID 74269Propanedioyl dichloride

Product 1

HCID 13755419HCID 13755419, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4-Nitroanthranilic acid (5.0 g, 26.6 mmol) was dissolved in dry dioxane (130 ml). To this solution, a solution of malonyl dichloride (1.45 g) in dry dioxane (5 ml) was added dropwise at room temperature. After stirring the mixture overnight, the precipitated crystals were collected by filtration, and washed with water and ether to give a pale yellow crystals of the title compound (2.58 g, 9.8%). m.p., 269°-270.5° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with water and ether

Sources & evidence

ORD record
ord-939a21499a704262b762abee7f8322ae
Source dataset
uspto-grants-1987_01
Patent number
US04634777

Reaction notes

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