4-Bromophenylhydrazine hydrochloride → HCID 19970994, compound

HRID 1414023Notes

Reaction equation

HRID 1414023 reaction equation
C(O[CH:4](OCC)[CH2:5][CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])C.Cl.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30]N)=[CH:26][CH:25]=1>C(O)(=O)C.O>[Br:23][C:24]1[CH:25]=[C:26]2[C:27](=[CH:28][CH:29]=1)[NH:30][CH:4]=[C:5]2[CH2:6][CH2:7][N:8]1[C:9](=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]1=[O:17]

Participants

5

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 128051862-(4,4-Diethoxybutyl)isoindoline-1,3-dione

Product 1

HCID 19970994HCID 19970994, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-[1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl]butanal diethyl acetal (11.6 g) was added with vigorous stirring to a solution of 4-bromophenylhydrazine hydrochloride (9.0 g) in 50% aqueous acetic acid (370 ml). The mixture was heated on a steam bath for 4 hours and was then diluted with water, while still hot, to 1 l. The mixture was cooled and an orange yellow precipitate was filtered off and dried in vacuo. The solid was boiled in ethanol (250 ml) for 1 hour and residual solid filtered off and dried to afford the title compound as a yellow solid (9.5 g) m.p. 206°-209° C. Crystallisation of a portion of this solid (0.5 g) from ethanol (25 ml) gave a sample (0.25 g) m.p. 208°-212° C.

Workup

  1. temperatureThe mixture was heated on a steam bath for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationan orange yellow precipitate was filtered off
  4. customdried in vacuo
  5. filtrationresidual solid filtered off
  6. customdried

Sources & evidence

ORD record
ord-b375734bfb7e45e798dadb526ba685f5
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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