Water → 1-(2-Hydrazino-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene

HRID 1740645Notes

Reaction equation

HRID 1740645 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH2:22][CH3:23])=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=3)[CH:11]=[C:10]([CH2:24][OH:25])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.C(Cl)Cl.O.O.[NH2:31][NH2:32]>>[NH:31]([C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH2:22][CH3:23])=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=3)[CH:11]=[C:10]([CH2:24][OH:25])[CH:9]=2)[CH:5]=[CH:4][N:3]=1)[NH2:32]

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 220073461-(2-Chloro-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene

Product 1

HCID 220073321-(2-Hydrazino-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene

Procedure

A suspension of 1-(2-chloro-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene (3.90 g) in hydrazine hydrate (17.8 ml) is refluxed for 9 hours. The mixture is stirred at room temperature for 10 minutes, and further stirred under ice-cooling for 10 minutes. To the mixture are added methylene chloride and water, and the methylene chloride layer is separated, washed, dried, and concentrated under reduced pressure to remove the solvent. The residue is dissolved in hot ethanol (20 ml), and allowed to cool overnight to give 1-(2-hydrazino-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene (3.19 g).

Workup

  1. temperatureis refluxed for 9 hours
  2. stirringfurther stirred under ice-
  3. temperaturecooling for 10 minutes
  4. customthe methylene chloride layer is separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. dissolutionThe residue is dissolved in hot ethanol (20 ml)
  10. temperatureto cool overnight

Sources & evidence

ORD record
ord-a689bc7de4e0433f8340f6eca084bf9f
Source dataset
uspto-grants-1999_10
Patent number
US05969140

Reaction notes

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