Hydrazine hydrate (1:1) → HCID 23471618, compound

HRID 128012Notes

Reaction equation

HRID 128012 reaction equation
Cl.O=[C:3]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH2:14][CH2:13]2)[CH:4]([CH3:9])[CH2:5][C:6](O)=[O:7].O.[NH2:20][NH2:21]>C(O)C>[CH3:9][CH:4]1[C:3]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH2:14][CH2:13]3)=[N:21][NH:20][C:6](=[O:7])[CH2:5]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70565681HCID 70565681, compound

Product 1

HCID 23471618HCID 23471618, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 27 g of 4-oxo-4-(indolin-5-yl)-3-methylbutanoic acid hydrochloride and 15 ml of hydrazine hydrate in 200 ml of ethanol was heated under reflux on a water bath for 2 hours. The reaction mixture was concentrated under reduced pressure and water was added to the residue. The precipitated crystals were filtered off, washed with water and recrystallized from ethanol to give 20 g of 5-(5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)indoline as white crystals, melting at 187°-189° C.

Workup

  1. temperatureunder reflux on a water bath for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water
  3. additionwas added to the residue
  4. filtrationThe precipitated crystals were filtered off
  5. washwashed with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3cfbcc037cc34e6b96199aaad13f8804
Source dataset
uspto-grants-1981_03
Patent number
US04258185

Reaction notes

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