Malononitrile → HCID 178509169, compound

HRID 254986Notes

Reaction equation

HRID 254986 reaction equation
N1[C:9]2[C:4](=[CH:5][C:6]([NH:10][N:11]=[C:12]([C:15]#[N:16])[C:13]#[N:14])=[CH:7][CH:8]=2)[CH:3]=N1.NC1C=C2C(=CC=1)[NH:23][N:22]=C2.C(#N)CC#N.O.[NH2:33][NH2:34]>>[NH:33]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][N:11]=[C:12]3[C:13]([NH2:14])=[N:23][N:22]=[C:15]3[NH2:16])=[CH:7][CH:8]=2)[CH:3]=[N:34]1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)HCID 880121H-Indazol-5-amineHCID 21955021HCID 21955021, compound

Product 1

HCID 178509169HCID 178509169, compoundYield 63%

Procedure

4-[(1H-Indazol-5-yl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 2-[(1H-indazol-5-yl)hydrazono]malononitrile (0.105 g, 0.5 mmol) which was derived from 5-aminoindazole (0.133 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, washed with ethanol, and dried to yield 0.076 g (63%) of the title compound as a brown solid; 1H NMR (ppm, 200 MHz, DMSO-d6) δ 6.0 (br s, 4H), 7.50 (d, 1H), 7.94 (d, 1H), 8.0 (s, 1H), 8.08 (s, 1H), 10.68 (br s, 1H), 13.08 (s, 1H).

Workup

  1. custom4-[(1H-Indazol-5-yl)hydrazono]-4H-pyrazole-3,5-diamine was prepared
  2. customThe resulting solid was isolated by filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-9d6e8f119dc241af9e64256a0ea9295f
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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