4-hydrazinylbenzamide → HCID 70571121, compound

HRID 1414039Notes

Reaction equation

HRID 1414039 reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].C(O[CH:15](OCC)[CH2:16][CH2:17][CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29])C>C(O)(=O)C>[O:29]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[N:19]1[CH2:18][CH2:17][CH2:16][CH:15]=[N:2][NH:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH2:9])=[O:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 47703774-hydrazinylbenzamideHCID 128051862-(4,4-Diethoxybutyl)isoindoline-1,3-dione

Product 1

HCID 70571121HCID 70571121, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-hydrazinobenzamide (0.26 g), in 25% aqueous acetic acid (20 ml) was added to 4-[1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]-butanal diethyl acetal (0.5 g). The mixture was heated on a steam bath for 2 hours and then cooled. The mixture was decanted to leave an oil which was triturated with methanol (3 ml). The solid that resulted was washed with water (5 ml) and dried in vacuo at 50° C. to give the title compound (0.55 g) as a yellow crystalline solid m.p. 147°-152° C. (decomp).

Workup

  1. temperatureThe mixture was heated on a steam bath for 2 hours
  2. temperaturecooled
  3. customThe mixture was decanted
  4. customto leave an oil which
  5. customwas triturated with methanol (3 ml)
  6. customThe solid that resulted
  7. washwas washed with water (5 ml)
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-f36c417021b74395878eb905d13fe09e
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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