Sodium Nitrite → 6-Nitro-1-phenyl-1,2-dihydroindazol-3-one

HRID 68674Notes

Reaction equation

HRID 68674 reaction equation
N[C:2]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:3]=1[C:4]([N:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:7])=O.N([O-])=[O:22].[Na+]>C(O)C.Cl.O1CCCC1.O>[N+:18]([C:16]1[CH:17]=[C:4]2[C:3]([C:2](=[O:22])[NH:7][N:6]2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:14][CH:15]=1)([O-:20])=[O:19]

Participants

7

Reactant 2

HCID 23668193Sodium NitriteHCID 674499692-amino-4-nitro-N-phenylbenzohydrazide

Product 1

HCID 569578826-Nitro-1-phenyl-1,2-dihydroindazol-3-one

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
72 °C

Procedure

Into a 1000-mL 4-necked round-bottom flask, was placed a solution of 2-amino-4-nitro-N-phenylbenzohydrazide (23 g, 84.56 mmol, 1.00 equiv) in ethanol (250 mL), 1N hydrogen chloride (250 mL), tetrahydrofuran (100 mL). To the resulting mixture was then added a solution of NaNO2 (17.5 g, 253.62 mmol, 3.00 equiv) in water (45 mL) dropwise with stirring at 72° C. in 40 min. The resulting solution was heated to reflux for 1 hr. The resulting mixture was then cooled to 25° C. The solids were collected by filtration to yield 6-nitro-1-phenyl-1,2-dihydroindazol-3-one as a brown solid. MS: 256 (MH+).

Workup

  1. customInto a 1000-mL 4-necked round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 1 hr
  4. temperatureThe resulting mixture was then cooled to 25° C
  5. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-bc405cb052eb4d1c932bae8aa20dfe32
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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