Ethyl Acetate → HCID 12805213, compound

HRID 1906220Notes

Reaction equation

HRID 1906220 reaction equation
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH2:13])=[O:12])=[CH:6][CH:5]=1)N.C(O[CH:17](OCC)[CH2:18][CH2:19][CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31])C.C(OCC)(=O)C>C(O)(=O)C>[O:31]=[C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29](=[O:30])[N:21]1[CH2:20][CH2:19][C:18]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]([NH2:13])=[O:12])[CH:8]=2)[NH:2][CH:17]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 128051862-(4,4-Diethoxybutyl)isoindoline-1,3-dioneHCID 20212863HCID 20212863, compound

Product 1

HCID 12805213HCID 12805213, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the crude 2-(4-hydrazinophenyl)acetamide hydrochloride (16.19 g) (contains 0.05 mol) and 4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butanal diethyl acetal (14.5 g) was heated under reflux in 25% aqueous acetic acid (1 l) for 30 min. The cooled mixture was poured into ethyl acetate (750 ml) the organic phase was separated and the aqueous phase was washed with ethyl acetate (250 ml). The combined organic extracts were washed with water (500 ml), dried (Na2SO4) and evaporated under reduced pressure. Water (500 ml) was added to the oily residue which solidified on stirring. The solid was collected by filtration, washed with water and dried. Crystallisation from ethyl acetate-methanol gave the title compound as pale yellow granules (11.9 g) m.p. 191°-3° C.

Workup

  1. temperaturewas heated
  2. customwas separated
  3. washthe aqueous phase was washed with ethyl acetate (250 ml)
  4. washThe combined organic extracts were washed with water (500 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. additionWater (500 ml) was added to the oily residue which
  8. filtrationThe solid was collected by filtration
  9. washwashed with water
  10. customdried
  11. customCrystallisation from ethyl acetate-methanol

Sources & evidence

ORD record
ord-cd2a2962879a4a68b75559ecc396222d
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

Loading…