Water → 3-Amino-5-nitroindazole

HRID 227694

Reaction equation

HRID 227694 reaction equation
[OH2:1].[NH2:2][NH2:3].Cl[C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:6]=1[C:7]#[N:8].[OH2:16]>N1C=CC=CC=1>[N+:13]([C:10]1[CH:9]=[C:6]2[C:5](=[CH:12][CH:11]=1)[NH:3][N:2]=[C:7]2[NH2:8])([O-:16])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 31366553-Amino-5-nitroindazoleYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrazine monohydrate (2.1 mL, 44 mmol) was added to a solution of 2-chloro-5-nitrobenzonitrile (7.30 g, 40 mmol) in pyridine (30 mL) and the mixture was heated to reflux overnight. The dark red solution was then cooled, poured into H2O and the resulting solid filtered and dried to give the title compound as a dark red powder (5.7 g, 80%). NMR 1H NMR (400 MHz, DMSO-D6) δ ppm 8.95 (d, J=2.0, 1H), 8.06 (dd, J=9.2, 2.0, 1H), 7.34 (d, J=9.2, 1H), 5.98 (br s, 2H) MS m/z 179.0 [M+H]+

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe dark red solution was then cooled
  4. filtrationthe resulting solid filtered
  5. customdried

Sources & evidence

ORD record
ord-d4f7d523609746209c9ba165007cd546
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Linked notes

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