Water → HCID 178515031, compound

HRID 1765366Notes

Reaction equation

HRID 1765366 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.O>C(O)(=O)C>[OH:15][C:10]1[C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13](=[O:14])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 7045914-Iodophenylhydrazine

Product 1

HCID 178515031HCID 178515031, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

4-Iodo phenyl hydrazine (8.97 g, 36.4 mmol) was added in one portion to a stirred mixture of phthalic anhydride (5.0 g, 33 mmol) in acetic acid (40 ml) at room temperature. The reaction mixture was heated to 125° C. for 2 hours, and then allowed to cool to room temperature. The suspension was poured into H2O (100 ml) and the resulting solid was removed by filtration. The mother liquor was acidified with conc. HCl. The resulting solid was collected by filtration and dried in vacuum to give the title compound (1.0 g, 8% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO) 11.91 (1H, br. s), 8.30 (1H, d), 7.91–8.03 (3H, m), 7.83 (2H, d), 7.51 (2H, d); MS (ESI+)=365.0 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. customthe resulting solid was removed by filtration
  3. filtrationThe resulting solid was collected by filtration
  4. customdried in vacuum

Sources & evidence

ORD record
ord-e58e4b9985844b848c5d95b2b193a5d9
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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