Stannous Chloride → HCID 14398233, compound

HRID 1709976Notes

Reaction equation

HRID 1709976 reaction equation
[CH3:1][O:2][C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[C:6]([CH2:17]Br)[O:5][N:4]=1.[Cl:19][Sn]Cl>CO.Cl>[CH3:1][O:2][C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])=[C:6]([CH2:17][Cl:19])[O:5][N:4]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 14398232HCID 14398232, compound

Product 1

HCID 14398233HCID 14398233, compoundYield 744.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 12 (0.3 g, 0.9 mmole) in MeOH (7ml) was added carefully a solution of SnCl2 2 H2O (0.72 g, 3.2 mmoles) in concentrated HCl (1 ml). The mixture was stirred at 80° C. for 21/2 hours and the solvent was evaporated. The residue was dissolved in an ice cooled solution of sodium hydroxyde (20 ml, 10N) and extracted with CHCl2. The combined organic extracts were dried, filtered and evaporated to give TLC pure 13 (1.6 g, 95%) as a yellow oil. CC (silica gel: 30 g; eluent: CH2Cl2) afforded 13 (1.55 g, 93) a TLC pure substance. 1H NMR 60 MHz (CDCl3) δ=3.75 (2H, broad s, exchangeable D20) 3.95 (3H, s) 4.4 (2H, s) 6.6-7.3 (4H, m). Mass spectrum, m/z -238/240 (M+).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in an ice cooled solution of sodium hydroxyde (20 ml, 10N)
  3. extractionextracted with CHCl2
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0eb59bc916524e5d834d2ab1fa47b964
Source dataset
uspto-grants-1990_08
Patent number
US04952573

Reaction notes

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