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

HRID 849608Notes

Reaction equation

HRID 849608 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[CH2:12][CH2:11][C:10](=O)[CH:9]1[CH2:8][N:7]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6]2)=[O:4].O.[NH2:31][NH2:32]>CO>[CH3:1][O:2][C:3]([C:5]12[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[CH2:12][CH2:11][C:10](=[N:31][NH2:32])[CH:9]1[CH2:8][N:7]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6]2)=[O:4]

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-500e7d7685da44958133c91bd1028815
Source dataset
uspto-grants-2000_01
Patent number
US06013662

Reaction notes

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