Stannous Chloride → HCID 86595903, compound

HRID 1296762Notes

Reaction equation

HRID 1296762 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:21]=[CH:20][C:10]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:9]([N+:22]([O-])=O)[CH:8]=2)[N:3]=1.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:22][C:9]1[CH:8]=[C:7]([C:4]2[N:3]=[C:2]([CH3:1])[O:6][N:5]=2)[CH:21]=[CH:20][C:10]=1[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 86595902HCID 86595902, compound

Product 1

HCID 86595903HCID 86595903, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of compound 58a (0.752 g, 2.25 mmol) in ethanol (12 mL) was added tin(II) chloride (1.62 g, 8.5 mmol). The reaction mixture was heated at 70° C. for 50 min, then cooled to rt. Saturated sodium bicarbonate solution was added. The resulting emulsion was filtered through Celite®, followed by ethyl acetate washes. The combined organic layers were washed with brine, dried, and concentrated to give compound 58b (0.57 g, 83%) as a yellow solid. ESI-MS m/e 305.5 (M+1).

Workup

  1. temperaturecooled to rt
  2. filtrationThe resulting emulsion was filtered through Celite®
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c01a62dcdbde417b9d2be1f877e15453
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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