Ethanol → HCID 86737391, compound

HRID 1732895Notes

Reaction equation

HRID 1732895 reaction equation
Cl.[CH3:2][N:3]([CH2:5][C:6]1[S:10][C:9]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23](=[O:24])[C:22]3C(=CC=CC=3)C2=O)=[CH:8][CH:7]=1)[CH3:4].[OH-:26].[Na+].[OH2:28].NN.[CH2:31]([OH:33])[CH3:32]>>[C:23]([OH:24])(=[O:33])[C:22]([OH:28])=[O:26].[C:31]([OH:24])(=[O:33])[C:32]([OH:28])=[O:26].[CH3:2][N:3]([CH2:5][C:6]1[S:10][C:9]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:8][CH:7]=1)[CH3:4]

Participants

5

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 70590708HCID 70590708, compound

Product 1

HCID 86737391HCID 86737391, compound

Procedure

N-[4-[5-(N,N-Dimethylaminomethyl)2-thienyl]butyl]1H-isoindole-1,3(2H)-dione hydrochloride (15.3 g) was treated with sodium hydroxide and extracted with ethyl acetate. Evaporation of the organic extracts gave an oil which was heated at reflux with hydrazine hydrate (2.5 g) in ethanol (100 ml) for 5 hr. Solvent was removed, the residue was basified and extracted with ethyl acetate. Addition of ethanolic oxalic acid gave the title compound as white crystals (9.58 g) m.p. 157.5°-159°. TLC silica/ethyl acetate, water, isopropanol, 0.88 ammonia, 25:8:15:2, Rf 0.20.

Workup

  1. extractionextracted with ethyl acetate
  2. customEvaporation of the organic extracts
  3. customgave an oil which
  4. temperaturewas heated
  5. customSolvent was removed
  6. extractionextracted with ethyl acetate
  7. additionAddition of ethanolic oxalic acid

Sources & evidence

ORD record
ord-abd1135d9aa2494180080b0e21548678
Source dataset
uspto-grants-1980_12
Patent number
US04239769

Reaction notes

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