Stannous chloride dihydrate → HCID 178433254, compound

HRID 1859073Notes

Reaction equation

HRID 1859073 reaction equation
[N:1]([C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]2[C:5]=1/[C:6](=[CH:17]/[C:18]1[NH:22][CH:21]=[N:20][C:19]=1[CH3:23])/[C:7](=[O:16])[NH:8]2)=[N+]=[N-].O.O.[Sn](Cl)Cl>CCO>[NH2:1][C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]2[C:5]=1/[C:6](=[CH:17]/[C:18]1[NH:22][CH:21]=[N:20][C:19]=1[CH3:23])/[C:7](=[O:16])[NH:8]2

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 178433256HCID 178433256, compound

Product 1

HCID 178433254HCID 178433254, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of (Z)-4-azido-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one (160 mg, 0.51 mmol) (from Example 43 above) in EtOH (10 mL), was added, at r.t., tin dichloride dihydrate. The heterogeneous mixture was heated at reflux for 6 h then cooled to r.t. The orange solid was collected by suction filtration, washed with ether and dried in a vacuum oven overnight to yield (Z)-4-amino-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one. (Yield 45 mg, 31%).

Workup

  1. additionwas added, at r.t.
  2. temperatureThe heterogeneous mixture was heated
  3. temperatureat reflux for 6 h
  4. filtrationThe orange solid was collected by suction filtration
  5. washwashed with ether
  6. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-26bd94f7066b4ae585021d3676186fb1
Source dataset
uspto-grants-2000_11
Patent number
US06153634

Reaction notes

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