Hydrochloric Acid → HCID 68835053, compound

HRID 490565Notes

Reaction equation

HRID 490565 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:19])[NH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:4][C:3]=1[N+:20]([O-])=O.Cl.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>>[NH2:20][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[Cl:1])[N:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[NH:7][C:6]2=[O:19]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 68831736HCID 68831736, compound

Product 1

HCID 68835053HCID 68835053, compoundYield 73.9%

Conditions

Temperature
85 °C

Procedure

To 6-chloro-1-(2-chloro-benzyl)-5-nitro-1,2-dihydro-indazol-3-one (0.49 g) was added HCl (37% aq.) solution (4 mL) followed by SnCl2.dihydrate (2.6 g). The mixture was heated to 85° C. for one hour. The reaction was then neutralized with sodium bicarbonate solution, filtered, and the filtrate extracted with EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and reduced in vacuo. Flash column chromatography of the residue over silica gel eluting with methylene chloride/methanol afforded the desired 5-amino-6-chloro-1-(2-chloro-benzyl)-1,2-dihydro-indazol-3-one (0.33 g) as a yellow solid. MS (ESI+): 308.3 [M+H]+).

Workup

  1. filtrationfiltered
  2. extractionthe filtrate extracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-535923116fd94c6a912cb7ffb7beda8c
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

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