Stannous Chloride → HCID 68153934, compound

HRID 1183247Notes

Reaction equation

HRID 1183247 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1.Cl[Sn]Cl>CC(O)=O.Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 68154114HCID 68154114, compound

Product 1

HCID 68153934HCID 68153934, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

The procedure described for the preparation of 7 was repeated using 300 mg (1.15 mmol) of 8 in 20 mL of glacial HOAc and 1.85 g (9.76 mmol, 8.5 equiv) of SnCl2 in 3 mL of conc HCl to afford, after stirring ca. 12 h at 25° C. and quenching with water, a precipitate. The precipitate was collected by filtration, washed with 5 mL of glacial acetic acid and suspended in 80 mL of water. The aqueous suspension was adjusted to pH 9-10 with NaOH and was extracted with Et2O. The combined ethereal extracts were washed with water, dried over anhydrous MgSO4, and concentrated. The product was recrystallized from hexane to afford 220 mg (83%) of 9 as colorless crystals: mp 74-75° C. NMR (DMSO-d6): δ 7.28 (d, 2H, J=8.8 Hz), 7.27-7.22 (m, 1H), 7.21 (d, 1H, J=16.8 Hz), 7.13-7.06 (m, 2H), 6.77 (d, 1H, J=16.8 Hz), 6.57 (d, 2H, J=8.8 Hz), 5.43 (s, 2H). 13C NMR (DMSO-d6): δ 160.35 (dd, J1=246.8 Hz, J2=8.0 Hz, two C), 150.06, 136.41 (t, J=7.9 Hz), 128.42 (two C), 127.99 (t, J=10.3 Hz), 124.68, 115.31 (t, J=15.1 Hz), 114.29 (two C), 112.33 (dd, J1=19.1 Hz, J2=6.3 Hz, two C), 108.84. MS: m/z (%) 232 (18), 231(100), 183 (13). Anal. Calcd for C14H11F2N: C, 72.72; H, 4.79. Found: C, 72.77; H, 4.83.

Workup

  1. customThe procedure described for the preparation of 7
  2. customto afford
  3. customquenching with water
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with 5 mL of glacial acetic acid
  6. extractionwas extracted with Et2O
  7. washThe combined ethereal extracts were washed with water
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated
  10. customThe product was recrystallized from hexane

Sources & evidence

ORD record
ord-1501893dbcc547cfabae9fd614df3397
Source dataset
uspto-grants-2014_03
Patent number
US08664276B2

Reaction notes

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