Trimellitic anhydride → 1,4-Dioxo-1,2,3,4-tetrahydrophthalazine-6-carboxylic acid

HRID 1783666Notes

Reaction equation

HRID 1783666 reaction equation
O.[NH2:2][NH2:3].[CH:4]1[C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]2[C:13](O[C:16](=[O:17])[C:6]=2[CH:5]=1)=[O:14]>CC(O)=O>[O:17]=[C:16]1[C:6]2[C:7](=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:4][CH:5]=2)[C:13](=[O:14])[NH:3][NH:2]1

Participants

4

Reactant 2

HCID 11089Trimellitic anhydrideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 3090561,4-Dioxo-1,2,3,4-tetrahydrophthalazine-6-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

Hydrazine hydrate (26 g, 0.52 mol) was added in one portion to a stirred mixture of 1,2,4-benzenetricarboxylic anhydride (100 g, 0.52 mol), in HOAc (1.0 L) at RT. The mixture was heated to 120° C. for 2 hours and then allowed to cool to RT. The solid was filtered, washed with water (250 ml) and dried in the vacuum oven at 50° C. for 20 hours to give the title compound (91 g, 85% yield).

Workup

  1. temperatureto cool to RT
  2. filtrationThe solid was filtered
  3. washwashed with water (250 ml)
  4. customdried in the vacuum oven at 50° C. for 20 hours

Sources & evidence

ORD record
ord-9d0f23005a0142b0931500d5b443f3f2
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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