Phthalaldehyde → HCID 1201585, compound

HRID 703201Notes

Reaction equation

HRID 703201 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]=O)[C:4]([CH:9]=[O:10])=[CH:3][CH:2]=1.[C:11]([C:16]1[CH:21]=[CH:20][C:19]([N:22]=C=O)=[CH:18][CH:17]=1)([O:13][CH2:14][CH3:15])=[O:12]>C(Cl)(Cl)Cl>[O:10]=[C:9]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH2:7][N:22]1[C:19]1[CH:18]=[CH:17][C:16]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 4807PhthalaldehydeHCID 589805Ethyl 4-isocyanatobenzoate

Product 1

HCID 1201585HCID 1201585, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of o-phthalicdicarboxaldehyde (17.54 g, 0.131 mol) and p-carbethoxyphenylisocyanate (25.0 g, 0.131 mol) is heated in an oil bath at 170° C. for 4.0 hours under nitrogen atmosphere. The hot melt is then slowly poured into CHCl3 (300 ml). The solution is then evaporated to dryness when a solid residue is obtained. The crude 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)benzoic acid, ethyl ester is triturated with isopropyl ether and then recrystallized from CH2Cl2 --isopropyl ether (1:1, 300 ml) to give white solid. Yield 5.07 g (13.8%); mp 182°-184° C.

Workup

  1. customThe solution is then evaporated to dryness when a solid residue
  2. customis obtained
  3. customThe crude 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)benzoic acid, ethyl ester is triturated with isopropyl ether
  4. customrecrystallized from CH2Cl2 --isopropyl ether (1:1, 300 ml)
  5. customto give white solid

Sources & evidence

ORD record
ord-fed5045726e948d0b98de4be756b25e0
Source dataset
uspto-grants-1991_01
Patent number
US04981865

Reaction notes

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