Hydrazine hydrate (1:1) → HCID 19834150, compound

HRID 2050792Notes

Reaction equation

HRID 2050792 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:8]([C:14]([O:16][CH2:17][CH2:18][N:19]2C(=O)C3=CC=CC=C3C2=O)=[O:15])=[C:9]([CH3:13])[NH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].O.NN>C(O)C>[CH2:1]([NH:3][C:4]([C:6]1[CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:8]([C:14]([O:16][CH2:17][CH2:18][NH2:19])=[O:15])=[C:9]([CH3:13])[NH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19834157HCID 19834157, compound

Product 1

HCID 19834150HCID 19834150, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 11.0 g (18.97 mmol) of N-ethyl 4-(2-benzyloxyphenyl)-1,4-dihydro-2,6-dimethyl-3-(2-phthalimido-ethoxycarbonyl)-pyridine-5-carboxamide (Example 28) and 95.0 mmol of hydrazine hydrate are heated under reflux in 100 ml of ethanol for 2 h. The solution is then cooled and the residue is filtered. The latter is subsequently washed with methylene chloride and the filtrate is concentrated in vacuo. The concentrated residue is then washed once with a 2 N solution of potassium hydroxide and then 3 times with water. The product is purified on a silica gel column using methylene chloride/methanol mixtures.

Workup

  1. temperatureThe solution is then cooled
  2. filtrationthe residue is filtered
  3. washThe latter is subsequently washed with methylene chloride
  4. concentrationthe filtrate is concentrated in vacuo
  5. washThe concentrated residue is then washed once with a 2 N solution of potassium hydroxide
  6. customThe product is purified on a silica gel column

Sources & evidence

ORD record
ord-e0361cbbe20247b89eb492e927f22253
Source dataset
uspto-grants-1991_05
Patent number
US05015650

Reaction notes

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