Sodium Hydroxide → HCID 18926409, compound

HRID 1378703Notes

Reaction equation

HRID 1378703 reaction equation
[Sn](Cl)Cl.[N+:4]([C:7]1[C:8](=[O:20])[N:9]([CH2:17][CH:18]=[CH2:19])[C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=1)([O-])=O.[OH-].[Na+]>Cl.C1COCC1>[NH2:4][C:7]1[C:8](=[O:20])[N:9]([CH2:17][CH:18]=[CH2:19])[C:10]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 18926421HCID 18926421, compound

Product 1

HCID 18926409HCID 18926409, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tin(II) chloride (924 mg, 4.09 mmol) in concentrated HCl (2.5 ml) was added dropwise to a stirred solution of 3-nitro-6-trifluoromethyl-1-allyl-2-pyridinone (127 mg, 0.512 mmol) in THF (6.5 ml) at -10° C. After 1 h at 0° C., the reaction was poured into a mixture of 50% sodium hydroxide and ice. The product was extracted into ethyl acetate, dried (Na2SO4), and evaporated in vacuo to give the title compound (106 mg): 1H NMR (CDCl3) selected signals at δ 4.63 (br s, 2H, NH2), 4.74 (d, J=5.4 Hz, 2H), 5.11-5.23 (m, 2H), 5.86-5.99 (m, 1H), 6.42 (d, J=7.7 Hz, 1H), 6.64 (d,J=7.7 Hz, 1H).

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-6fab002b257f471495f65f9afdb08811
Source dataset
uspto-grants-1997_09
Patent number
US05668289

Reaction notes

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