Acetic Acid → HCID 22007359, compound

HRID 613020Notes

Reaction equation

HRID 613020 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[C:11]([CH2:23][OH:24])[C:10]=2[CH2:25][OH:26])[CH:6]=[CH:5][N:4]=1)[NH2:2].[C:27](O)(=[O:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:27]([NH:2][NH:1][C:3]1[CH:8]=[C:7]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[C:11]([CH2:23][OH:24])[C:10]=2[CH2:25][OH:26])[CH:6]=[CH:5][N:4]=1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 22007376HCID 22007376, compound

Product 1

HCID 22007359HCID 22007359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-hydrazino-4-pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (2.0 g) and acetic acid (20 ml) is stirred at room temperature for 96 hours. After the reaction is complete, to the mixture are added methylene chloride and an aqueous potassium carbonate solution. The methylene chloride layer is separated, concentrated under reduced pressure, and the residue is crystallized from chloroform to give 1-[2-(2-acetylhydrazino)pyridin-4-yl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (0.84 g), which is listed in Table 10.

Workup

  1. customThe methylene chloride layer is separated
  2. concentrationconcentrated under reduced pressure
  3. customthe residue is crystallized from chloroform

Sources & evidence

ORD record
ord-59a4f45a6fc84a8e8c6290482806f619
Source dataset
uspto-grants-1999_12
Patent number
US06005106

Reaction notes

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