Stannous Chloride → HCID 10012917, compound

HRID 1190914Notes

Reaction equation

HRID 1190914 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[F:14])[CH3:2].Cl[Sn]Cl>C1COCC1.Cl>[CH2:1]([N:3]([CH2:4][C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[F:14])[CH2:15][CH3:16])[CH3:2]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 10331271HCID 10331271, compound

Product 1

HCID 10012917HCID 10012917, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diethyl-(2-fluoro-5-nitro-benzyl)-amine (0.155 mg, 0.69 mmoles) in THF (20 mL) was added a solution of SnCl2 (520 mg, 2.74 mmoles) in THF (5 mL) and HCl 1M (2.1 mL). The reaction mixture was refluxed for 8 h and concentrated. Saturated solution of NaHCO3 was added until pH8. Aqueous layer was extracted with CH2Cl2 (5×50 mL). The organic layer was dried over MgSO4, filtered, evaporated. Expected compound was precipited with MeOH and purified by TLC DCM/MeOH/NH4OH//9/1/0.2) and obtained as a yellow oil (98 mg, 73% yield). MALDI-TOF: m/z 197.2 [M+H]+. 1H NMR (300 MHz, CDCl3) δ6.80; (dd, J=8.7 Hz and 8.7 Hz, 1H), 6.75; (dd, J=5.7 Hz and 3.0, 1H), 6.49; (ddd, J=8.7 Hz, 3.9 Hz and 3.0 Hz, 1H), 3.65-3.75; (s large, 2H), 3.57; (s, 2H), 2.57; (q, J=7.2 Hz, 4H), 1.07; (t, J=7.2 Hz, 6H). 13C NMR (75 MHz, CDCl3) δ118.2; (CH, d, J=3.8 Hz), 116.4; (CH, d, J=23.3 Hz), 115.7; (CH, d, J=7.9 Hz), 49.8; (CH2), 47.3; (CH2), 12.4; (CH3).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. concentrationconcentrated
  3. additionSaturated solution of NaHCO3 was added until pH8
  4. extractionAqueous layer was extracted with CH2Cl2 (5×50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by TLC DCM/MeOH/NH4OH//9/1/0.2) and

Sources & evidence

ORD record
ord-4f9de31a34b64ab8beb527ae9e1aea95
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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