Sodium Hydroxide → HCID 66746819, compound

HRID 711828Notes

Reaction equation

HRID 711828 reaction equation
[C:1]([C:3]1[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH2:6][C:7]([CH3:21])([CH3:20])[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:9])#[N:2].O.O.Cl[Sn]Cl.[OH-].[Na+]>COCCOCCOC.Cl>[NH2:26][C:25]1[C:3]([C:1]#[N:2])=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][CH2:6][C:7]([CH3:21])([CH3:20])[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 66746948HCID 66746948, compound

Product 1

HCID 66746819HCID 66746819, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8150DiglymeSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(2-cyano-3-nitrophenoxy)-N-(4-methoxybenzyl)-2,2-dimethyl-propanamide (1.15 g, 3.0 mmol) (Example 220c) in diglyme (30 mL) was added dropwise a solution of SnCl2.2H2O (2.03 g, 9.0 mmol) in concentrated HCl (15 mL) at 0° C. The reaction mixture was then stirred at 0° C. for another 1 hr. The reaction solution was neutralized with 2 N NaOH at 0° C., and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting with 50% EtOAc in hexanes to give the title compound as a white solid (0.91 g) in 86% yield. MS 354 (MH+).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by chromatography on silica gel eluting with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-7f4f4be0721e4001be820b5f53edd267
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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