Hydrazine hydrate (1:1) → HCID 12805224, compound

HRID 1906237Notes

Reaction equation

HRID 1906237 reaction equation
O=C1C2C(=CC=CC=2)[C:4](=[O:11])[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.[OH2:27].NN>C(O)C>[C:20]1([CH2:23][O:27][C:4]([NH:3][CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]([NH2:26])=[O:25])[CH:21]=3)[NH:16][CH:15]=2)=[O:11])[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12805213HCID 12805213, compound

Product 1

HCID 12805224HCID 12805224, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-acetamide (17.55 g) and hydrazine hydrate (12 ml) in ethanol (700 ml) was heated at reflux for 2 h. The resulting suspension was cooled to ambient temperature and all the solvent was evaporated in vacuo. The resulting yellow solid was dissolved in dilute sodium hydroxide (250 ml) and tetrahydrofuran (100 ml) and treated with benzylchloroformate (21 ml) at 5°. Stirring was continued for 1 h at ambient temperature, reaction mixture extracted with ethylacetate (4×200 ml), dried (MgSO4) and solvent removed to give crude product as an oil which on trituration with ethylacetate gave the title compound as a white solid (6.4 g) m.p. 124°-5°.

Workup

  1. temperatureat reflux for 2 h
  2. customall the solvent was evaporated in vacuo
  3. dissolutionThe resulting yellow solid was dissolved in dilute sodium hydroxide (250 ml)
  4. additiontetrahydrofuran (100 ml) and treated with benzylchloroformate (21 ml) at 5°
  5. customreaction mixture
  6. extractionextracted with ethylacetate (4×200 ml)
  7. dry with materialdried (MgSO4) and solvent
  8. customremoved
  9. customto give crude product as an oil which on trituration with ethylacetate

Sources & evidence

ORD record
ord-1ff5a32c5a6648569206b4f8ee29b681
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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