Water → HCID 59548936, compound

HRID 1946835Notes

Reaction equation

HRID 1946835 reaction equation
O.O.[Sn](Cl)Cl.[F:6][C:7]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:8]=1[O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=1[N+:18]([O-])=O.CCOC(C)=O.O>CCO.Cl>[NH2:18][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:10]=1[O:9][C:8]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:7]=1[F:6])[C:14]#[N:15]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 59548943HCID 59548943, compound

Product 1

HCID 59548936HCID 59548936, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of Tin (II) chloride dihydrate (18.238 g, 81.00 mmol) in EtOH (65.00 mL) and HCl (12 M, 10.00 mL) was stirred at 70° C. until the solution became clear. Compound 21 (5.60 g, 20.28 mmol) was then added over 10 min. The solution was kept slightly refluxing during addition. The reaction was monitored with TCL (25% EtOAc in hexanes, Rf=0.65). The reaction was complete after refluxing for 1.5 hrs, as indicated by the absence of the starting material (TLC). Water (80 mL) was added and the resulting solution was allowed to cool to room temperature. The desired product was precipitated out as a white solid during cooling. The mixture was further cooled and stirred for 30 min at 15° C. The resulting precipitation was collected via filtration under vacuum, washed with water, and dried under vacuum to yield compound 22 as a white solid (3.60 g, 99.0% HPLC purity, 63% yield). 1H NMR (500 MHz, DMSO-d6): δ 7.44 (m, 1H), 7.09 (m, 2H), 7.04 (m, 1H), 6.92 (dd, J1=2 Hz, J2=8 Hz, 1H), 6.78 (d, J=8 Hz, 1H), 5.65 (s, 2H).

Workup

  1. temperatureThe solution was kept slightly refluxing during addition
  2. temperatureafter refluxing for 1.5 hrs
  3. temperatureto cool to room temperature
  4. customThe desired product was precipitated out as a white solid
  5. temperatureduring cooling
  6. temperatureThe mixture was further cooled
  7. stirringstirred for 30 min at 15° C
  8. customThe resulting precipitation
  9. filtrationwas collected via filtration under vacuum
  10. washwashed with water
  11. customdried under vacuum

Sources & evidence

ORD record
ord-613239ce996f42d39f35e61f39746f90
Source dataset
uspto-grants-2013_03
Patent number
US08399456B2

Reaction notes

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