Sodium Hydroxide → HCID 178467356, compound

HRID 885424Notes

Reaction equation

HRID 885424 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:3]=1[NH2:4].[OH-].[Na+].[CH2:14]([O:16][C:17](OCC)(OCC)OCC)[CH3:15]>C(O)C>[Cl:1][C:2]1[C:3]2[NH:4][C:17]([O:16][CH2:14][CH3:15])=[N:9][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66213Tetraethyl orthocarbonateHCID 698552-Chloro-6-nitroaniline

Product 1

HCID 178467356HCID 178467356, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

2-Chloro-6-nitroaniline (3.45 g, 20.0 mmol) and stannous chloride dihydrate (18.05 g, 80.0 mmol) were heated under reflux in ethanol (80 mL) for 3 hr. The reaction mixture was neutralized with aqueous sodium hydroxide solution, and the precipitate was filtered off. The filtrate was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was mixed with tetraethoxymethane (10 mL, 47.7 mmol) and the mixture was stirred at 130° C. for 12 hr. The reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate=50/50) to give the title compound (1.38 g, 35%).

Workup

  1. filtrationthe precipitate was filtered off
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-6e1933e1b30e41918fc506baf6325c5e
Source dataset
uspto-grants-2012_08
Patent number
US08242151B2

Reaction notes

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