Hydrochloric Acid → HCID 68831736, compound

HRID 490564Notes

Reaction equation

HRID 490564 reaction equation
Cl[N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[C:4](=[O:14])[NH:3]1.C([O-])([O-])=O.[K+].[K+].[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Br.[ClH:30]>O>[Cl:30][C:8]1[CH:9]=[C:10]2[C:5]([C:4](=[O:14])[NH:3][N:2]2[CH2:24][C:23]2[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=2[Cl:21])=[CH:6][C:7]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 86604125HCID 86604125, compound

Product 1

HCID 68831736HCID 68831736, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Chloro-5-nitro-1,2-dihydro-indazol-3-one (prepared in analogy to Org. Synth. 1949, 29, 54 or Chem Ber. 1942, 75, 1104 from 4-chloro-2-fluoro-5-nitro-benzoic acid over two steps) (0.6 g) was suspended in water (5 mL) and 2N K2CO3 (aq.) (1 g) was added to the flask and the mixture was heated to 50° C. for 10 minutes. 2-Chlorobenzylbromide (0.40 g) was then added dropwise. The reaction was stirred overnight and was neutralized with 2 N HCl (aq.) while cooling in an ice bath. The precipitate was collected by filtration and triturated with diethylether to afford pure desired 6-chloro-1-(2-chloro-benzyl)-5-nitro-1,2-dihydro-indazol-3-one as a brown solid. MS (ESI−:336.3[M−H]−).

Workup

  1. temperaturewhile cooling in an ice bath
  2. filtrationThe precipitate was collected by filtration
  3. customtriturated with diethylether

Sources & evidence

ORD record
ord-c20c62834ee04242b1eb7e9c6d2da3d7
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

Loading…