Hydrochloric Acid → HCID 20212876, compound

HRID 1906221Notes

Reaction equation

HRID 1906221 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]([NH2:26])=[O:25])[CH:21]=2)[NH:16][CH:15]=1.O.NN.CO.[ClH:32]>C(O)C.C(OCC)(=O)C>[ClH:32].[NH2:3][CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]([NH2:26])=[O:25])[CH:21]=2)[NH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 12805213HCID 12805213, compound

Product 1

HCID 20212876HCID 20212876, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-acetamide (8.0 g) in ethanol (500 ml) containing hydrazine hydrate (5.76 g), was heated under reflux for 2 h. The solvent was removed by evaporation, the residue was suspended in ethyl acetate (500 ml) and washed with saturated potassium carbonate solution (300 ml). The organic phase was separated and the aqueous phase again extracted with ethyl acetate (200 ml). Evaporation of the dried (Na2SO4) combined organic extracts gave an off-white solid. This was dissolved in ethyl acetate (90 ml) containing methanol (10 ml) and ethereal hydrogen chloride was added until no more solid deposited. Crystallisation from ethyl acetate-methanol gave the title compound as off-white granules (3.2 g) m.p. 225°-7° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. customThe solvent was removed by evaporation
  4. washwashed with saturated potassium carbonate solution (300 ml)
  5. customThe organic phase was separated
  6. extractionthe aqueous phase again extracted with ethyl acetate (200 ml)
  7. customEvaporation of the
  8. dry with materialdried (Na2SO4)
  9. customgave an off-white solid
  10. additionwas added until no more solid
  11. customCrystallisation from ethyl acetate-methanol

Sources & evidence

ORD record
ord-14204eefbe564558a146223f98862f47
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

Loading…