Hydrazine hydrate (1:1) → HCID 86755059, compound

HRID 324668Notes

Reaction equation

HRID 324668 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2([C:17]([O:19][CH3:20])=[O:18])[CH:10]([C:11](=O)[CH2:12][CH2:13][CH:14]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:31][NH2:32]>CO>[CH2:1]([N:8]1[CH2:16][C:15]2([C:17]([O:19][CH3:20])=[O:18])[CH:10]([C:11](=[N:31][NH2:32])[CH2:12][CH2:13][CH:14]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86755060HCID 86755060, compound

Product 1

HCID 86755059HCID 86755059, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 166.6 g (0.424 mol) of methyl (3aRS,4SR,7aRS)-2-benzyl-4-(2-methoxyphenyl)-7-oxo-octahydroisoindole-3a-carboxylate and of 84.5 g (1.69 mol) of hydrazine hydrate in 2.8 dm3 of methanol is brought to reflux for two hours. After concentrating the methanol under reduced pressure, the residue was taken up in 2 dm3 of dichloromethane, washed with four times 1 dm3 of distilled water, dried over magnesium sulphate and concentrated under reduced pressure. 175.2 g of methyl (3aRS,4SR,7aRS)-2-benzyl-7-hydrazono-4-(2-methoxyphenyl)octahydroisoindole-3a-carboxylate were thus obtained in the form of a yellow oil, the characteristics of which were as follows:

Workup

  1. temperatureto reflux for two hours
  2. concentrationAfter concentrating the methanol under reduced pressure
  3. washwashed with four times 1 dm3 of distilled water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8df6dbfdd65e419fb70f8bf5aba22cce
Source dataset
uspto-grants-2001_04
Patent number
US06218406B1

Reaction notes

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