2-Naphthylamine → HCID 178509167, compound

HRID 254951Notes

Reaction equation

HRID 254951 reaction equation
C1C2C(=CC=CC=2)C=CC=1N[N:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15].[NH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1.C(#N)CC#N.O.[NH2:35][NH2:36]>>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[NH:18][N:12]=[C:13]1[C:14]([NH2:15])=[N:36][N:35]=[C:16]1[NH2:17]

Participants

5

Reactant 4

HCID 70572-NaphthylamineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 13169394HCID 13169394, compound

Product 1

HCID 178509167HCID 178509167, compound

Procedure

4-(naphthalen-2-ylhydrazono)-4H-pyrazole-3,5-diamine was prepared using 110 mg (0.5 mmol) of 2-[(naphthalen-2-yl)hydrazono]malononitrile, which was derived from 2-aminonaphthalene (143 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. The hydrazine hydrate was added to the solution at a temperature of 75° C. despite the fact that the starting material had not fully dissolved. The solution cleared briefly and then a precipitate formed. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 86 mg (67%) of the compound as a tan coloured solid.

Workup

  1. dissolutionhad not fully dissolved
  2. customa precipitate formed
  3. customThe resulting solid was isolated by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-e13936c49cab4c85959d595aca2009b9
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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