Hydrochloric Acid → HCID 22933647, compound

HRID 1269852Notes

Reaction equation

HRID 1269852 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[CH3:19].Cl.F[B-](F)(F)F.[NH4+].[N:27]([O-])=O.[Na+].[Cl-].[Na+].C([O-])(=O)C.[K+]>O.C1OCCOCCOCCOCCOCCOC1>[NH:1]1[C:2]2[C:3](=[CH:4][C:5]([O:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9]([O:11][CH3:12])=[O:10])=[CH:17][CH:18]=2)[CH:19]=[N:27]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium Chloride2×HCID 517044Potassium AcetateHCID 9964072Ammonium fluoroborateHCID 22933360Methyl 2-(4-amino-3-methylphenoxy)benzoateHCID 23668193Sodium Nitrite

Product 1

HCID 22933647HCID 22933647, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 962WaterSolvent

Procedure

Methyl 2-(4-amino-3-methylphenoxy)benzoate (500 mg, 1.94 mmol) was suspended in water (5.7 ml), followed by adding thereto concentrated hydrochloric acid (1.0 ml) and ammonium tetrafluoroborate (693 mg) at 0° C. An aqueous sodium nitrite solution (134 mg/1 ml) was added dropwise to the suspension. A saturated aqueous sodium chloride solution was added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting dark-blue oil was dissolved in chloroform (15 ml), and potassium acetate (381 mg, 3.88 mmol) and 18-crown-6 (15 mg) were added thereto at room temperature and then stirred for 2 hours. To the resulting suspension was added a saturated aqueous sodium chloride solution, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic layer dried was concentrated and then purified by a silica gel column chromatography (chloroform/methanol=70/1) to obtain methyl 2-(1H-indazol-5-yloxy)benzoate (157 mg, two steps 30%).

Workup

  1. additionby adding
  2. customat 0° C
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. dissolutionThe resulting dark-blue oil was dissolved in chloroform (15 ml)
  7. extractionfollowed by extraction with chloroform
  8. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe organic layer dried
  11. concentrationwas concentrated
  12. custompurified by a silica gel column chromatography (chloroform/methanol=70/1)

Sources & evidence

ORD record
ord-55a74f5526424cd4996aae02d9b42842
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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