2-(4,4-Diethoxybutyl)isoindoline-1,3-dione → HCID 12805220, compound

HRID 1906233Notes

Reaction equation

HRID 1906233 reaction equation
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1)N.C(O[CH:16](OCC)[CH2:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])C>C(O)(=O)C>[O:30]=[C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28](=[O:29])[N:20]1[CH2:19][CH2:18][C:17]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]#[N:12])[CH:8]=2)[NH:2][CH:16]=1

Participants

4

Reactant 2

HCID 128051862-(4,4-Diethoxybutyl)isoindoline-1,3-dioneHCID 18944276HCID 18944276, compound

Product 1

HCID 12805220HCID 12805220, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-hydrazino phenylacetonitrile hydrochloride (3.15 g) and 4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butanal diethyl acetal (4.95 g) in acetic acid (25%, 150 ml) was refluxed for 2 h, cooled to 25°, precipitate filtered, washed with water (2×20 ml) and ether (100 ml). The crude product was obtained as a dark solid (4.5 g) which was triturated with ethyl acetate to give the title compound (3.16 g) m.p. 185°-186°.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturecooled to 25°
  3. filtrationprecipitate filtered
  4. washwashed with water (2×20 ml) and ether (100 ml)

Sources & evidence

ORD record
ord-1f8d49b77272466b92b1cdbbdd72c59f
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

Loading…