Ethyl Acetate → HCID 12805217, compound

HRID 1906225Notes

Reaction equation

HRID 1906225 reaction equation
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:6][CH:5]=1)N.[O:16]=[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[N:18]1[CH2:27][CH2:28][CH2:29][CH:30]=O.C(OCC)(=O)C>C(O)(=O)C>[O:16]=[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[N:18]1[CH2:27][CH2:28][C:29]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH:8]=2)[NH:2][CH:30]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 20212868HCID 20212868, compound

Product 1

HCID 12805217HCID 12805217, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(4-hydrazinophenyl)-N,N-dimethylacetamide hydrochloride (0.875 g, contains 0.00315 mol) and 4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butanal, diethyl acetal (0.873 g) was heated under reflux in 25% aqueous acetic acid (100 ml) for 30 min. The mixture was poured into ethyl acetate (150 ml) and the aqueous phase was separated. This was washed with ethyl acetate (150 ml) and the organic extracts were combined. The yellow solution was washed successively with water (150 ml) 8% sodium bicarbonate solution (150 ml) and finally water (150 ml). Evaporation of the dried (Na2SO4) solvent gave a yellow solid which crystallised from propan-2-ol to give the title compound as a pale yellow powder (0.91 g) m.p. 193°-4° C.

Workup

  1. temperaturewas heated
  2. customthe aqueous phase was separated
  3. washThis was washed with ethyl acetate (150 ml)
  4. washThe yellow solution was washed successively with water (150 ml) 8% sodium bicarbonate solution (150 ml) and finally water (150 ml)
  5. customEvaporation of the
  6. dry with materialdried (Na2SO4) solvent
  7. customgave a yellow solid which
  8. customcrystallised from propan-2-ol

Sources & evidence

ORD record
ord-9297fea8b7694e5d9a39e35b85f62fa9
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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