Hydrazine hydrate (1:1) → HCID 13096733, compound

HRID 1632187Notes

Reaction equation

HRID 1632187 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([C@H:12]3[CH2:15][CH2:14][C@H:13]3[C:16](O)=[O:17])=O)=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:19].O.[NH2:21][NH2:22]>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:12]4[CH:13]([C:16](=[O:17])[NH:21][N:22]=3)[CH2:14][CH2:15]4)=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:19]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22827913HCID 22827913, compound

Product 1

HCID 13096733HCID 13096733, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.22 g (0.02 mole) of cis-2-(indolin-2-on-5-oyl)cyclobutanecarboxylic acid are refluxed with 1.1 g (0.022 mole) of hydrazine hydrate and 50 ml of ethanol for 11 hours. The solid is filtered off with suction at room temperature and recrystallized from dimethylformamide/water to give 4.7 g (92%) of 2-(indolin-2-on-5-yl)-3,4-diazabicyclo[4.2.0]oct-2-en-5-one of melting point 309°-312° C.

Workup

  1. filtrationThe solid is filtered off with suction at room temperature
  2. customrecrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-25623125f52e40bdbaf3bbf5e77652c5
Source dataset
uspto-grants-1984_10
Patent number
US04474785

Reaction notes

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