Ethanol → HCID 67447670, compound

HRID 68668Notes

Reaction equation

HRID 68668 reaction equation
N[C:2]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].C(O)C.N([O-])=O.[Na+]>Cl.O>[Br:18][C:16]1[CH:15]=[C:14]2[C:3]([C:4](=[O:5])[NH:6][N:7]2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:2][CH:17]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 23668193Sodium NitriteHCID 674466302-amino-4-bromo-N'-phenylbenzohydrazide

Product 1

HCID 67447670HCID 67447670, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
76 °C

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 2-amino-4-bromo-N′-phenylbenzohydrazide (4 g, 13.07 mmol, 1.00 equiv) in 1N HCl:Ethanol=1:1 (40 mL). The resulting solution was heated to 76° C. The solid dissolved to yield red solution. To the resulting mixture was then added a solution of NaNO2 (2.7 g, 39.13 mmol, 3.00 equiv) in water (5 mL) dropwise with stirring at 76° C. The resulting solution was stirred for 1 h at 76° C. in an oil bath. The resulting mixture was cooled to 20° C. with a water bath. The solids were collected by filtration, washed with water (2×40 mL), then dried in an oven under reduced pressure to yield 6-bromo-1-phenyl-1,2-dihydroindazol-3-one as a red solid. MS: 288 (MH+).

Workup

  1. customInto a 100-mL 3-necked round-bottom flask, was placed
  2. dissolutionThe solid dissolved
  3. customto yield red solution
  4. stirringThe resulting solution was stirred for 1 h at 76° C. in an oil bath
  5. temperatureThe resulting mixture was cooled to 20° C. with a water bath
  6. filtrationThe solids were collected by filtration
  7. washwashed with water (2×40 mL)
  8. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-ff97c786053b4c80aa8c183473692a5b
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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