1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → HCID 12805187, compound

HRID 1906217Notes

Reaction equation

HRID 1906217 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH:15]=O.Cl.[NH:18]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:22][CH:21]=1)N>C(O)C.C(O)(=O)C.O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][C:27]([OH:29])=[O:28])[CH:24]=2)[NH:18][CH:15]=1

Participants

6

Reactant 2

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 15618594(4-Hydrazinophenyl)acetic acid hydrochloride

Product 1

HCID 12805187HCID 12805187, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butanal, diethyl acetal (36 g) in absolute ethanol (125 ml) was added to a solution of 4-hydrazinobenzene acetic acid, hydrochloride (25 g) in 25% aqueous acetic acid (640 ml) heated to 80° under nitrogen. The mixture was heated at 70°-80° for 2.75 h and the solvent was removed under reduced pressure to give a red oil. This was diluted with water and extracted with ethyl acetate (5×250 ml). A gummy solid insoluble in either phase was collected and triturated with ethanol to give the title compound as a beige solid (7.4 g). The organic extracts were dried (MgSO4) and concentrated to an oil which was taken up in chloroform and treated with diethyl ether to give a second crop as a yellow solid (13.1 g). A sample (0.5 g) of this material was purified by column chromatography (Whatman MFC silica, 25 g) and elution with ethyl acetate--light petroleum (1:1) gave the title compound as a yellow solid (0.35 g) m.p. 189°-191.5°.

Workup

  1. temperatureheated to 80° under nitrogen
  2. temperatureThe mixture was heated at 70°-80° for 2.75 h
  3. customthe solvent was removed under reduced pressure
  4. customto give a red oil
  5. extractionextracted with ethyl acetate (5×250 ml)
  6. customA gummy solid insoluble in either phase was collected
  7. customtriturated with ethanol

Sources & evidence

ORD record
ord-e695ebed57c444e08138e2aa419d8ad9
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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