Malononitrile → HCID 178509168, compound

HRID 2095153Notes

Reaction equation

HRID 2095153 reaction equation
N1C2C(=CC(N[N:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15])=CC=2)C=CC=1.[NH2:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][CH:23]=[CH:22]2.C(#N)CC#N.O.[NH2:35][NH2:36]>>[N:25]1[C:26]2[C:21](=[CH:20][C:19]([NH:18][N:12]=[C:13]3[C:14]([NH2:15])=[N:36][N:35]=[C:16]3[NH2:17])=[CH:28][CH:27]=2)[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 113736-AminoquinolineHCID 24654Hydrazine hydrate (1:1)HCID 21955006HCID 21955006, compound

Product 1

HCID 178509168HCID 178509168, compoundYield 20%

Procedure

4-(Quinolin-6-ylhydrazono)-4H-pyrazole-3,5-diamine was prepared using 2-(quinolin-6-ylhydrazono)malononitrile (0.11 g, 0.5 mmol) which was derived from 6-aminoquinoline (0.144 g, 1.0 mmol) and malononitrile (1.5 mmol) in a manner similar to that described in Example 2, and hydrazine hydrate. The resulting solid was isolated by filtration and purified by flash chromatography to yield 0.025 g (20%) of the title compound as an orange solid; 1H NMR (ppm, 200 MHz, DMSO-d6) δ 5.95 (br s, 2H), 6.45 (br s, 2H), 7.40-7.55 (m, 1H), 7.98 (d, 1H), 8.10 (s, 1H), 8.20-8.40 (m, 2H), 8.79 (d, 1H), 10.35 (brs, 1H).

Workup

  1. custom4-(Quinolin-6-ylhydrazono)-4H-pyrazole-3,5-diamine was prepared
  2. customThe resulting solid was isolated by filtration
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d3ffda6c94a9488ea32e320f308e71dc
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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