Hydrochloric Acid → HCID 16775466, compound

HRID 1591862Notes

Reaction equation

HRID 1591862 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)=[O:5].O.O.Cl[Sn]Cl.Cl.[OH-].[Na+]>C(O)C>[NH2:14][C:9]1[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:2]=2[Cl:1])[CH:12]=[CH:11][C:10]=1[F:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 26696954HCID 26696954, compound

Product 1

HCID 16775466HCID 16775466, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Add 2-chloro-4-fluoro-N-(4-fluoro-3-nitrophenyl)benzamide (Preparation 11, 1 g, 3.2 mmol) to a warm solution (55° C.) of SnCl2.2H2O (3.6 g, 16 mmol) in ethanol (25 mL). Add concentrated HCl (25 mL). Stir and heat the mixture at 60° C. for 30 min. Cool and then basicify the mixture to pH 14 with aqueous NaOH. Extract the product three times with ethyl acetate (3×150 mL). Combine the organic layers and dry over anhydrous sodium sulfate. Evaporate the solvent under reduced pressure. Further purify the residue by chromatography on silica gel, using a gradient of 10–50% ethyl acetate in hexanes to obtain the title intermediate (800 mg, 89% yield): mass spectrum (ion spray): m/z=283.0 (M+1).

Workup

  1. temperatureCool
  2. extractionExtract the product three times with ethyl acetate (3×150 mL)
  3. dry with materialCombine the organic layers and dry over anhydrous sodium sulfate
  4. customEvaporate the solvent under reduced pressure
  5. customFurther purify the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-4b6748e2ab8e4e98902d5442007e82cc
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Reaction notes

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