Stannous Chloride → HCID 117601490, compound

HRID 1773759Notes

Reaction equation

HRID 1773759 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:13]=[C:12]([N+:14]([O-])=O)[C:10]([NH2:11])=[C:9]([I:17])[CH:8]=2)=[C:5]([CH3:18])[O:4][N:3]=1.Cl[Sn]Cl>CCO>[CH3:1][C:2]1[C:6]([C:7]2[CH:13]=[C:12]([NH2:14])[C:10]([NH2:11])=[C:9]([I:17])[CH:8]=2)=[C:5]([CH3:18])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 117601618HCID 117601618, compound

Product 1

HCID 117601490HCID 117601490, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

4-(3,5-dimethylisoxazol-4-yl)-2-iodo-6-nitroaniline (0.9 g, 2.5 mmol) was added to EtOH (50 ml), to the mixture were added SnCl2 (2.4 g, 12.5 mmol). The reaction mixture was stirred at 75° C. for 7 h. The solvent was evaporated and then the residue was dissolved in EtOAc (100 ml) and washed with 1N NaOH (100 ml×3). The organic solvent was evaporated and the residue was dissolved in DCM and purified with combi-flash column chromatography (product came out at 60% EtOAc/Hexane) to afford 5-(3,5-dimethylisoxazol-4-yl)-3-iodobenzene-1,2-diamine. LCMS m/z [M+H]+ C11H12IN3O requires: 330.00. Found 330.03 1H NMR (400 MHz, CD3OD) δ2.21 (s, 3H), 2.39 (s, 3H), 7.16 (d, 1H), 7.62 (d, 1H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc (100 ml)
  3. washwashed with 1N NaOH (100 ml×3)
  4. customThe organic solvent was evaporated
  5. dissolutionthe residue was dissolved in DCM
  6. custompurified with combi-flash column chromatography (product

Sources & evidence

ORD record
ord-c5fa156524d04e83a64889a895464c73
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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