Hydrochloric Acid → HCID 23149649, compound

HRID 2410310Notes

Reaction equation

HRID 2410310 reaction equation
Cl.[Sn](Cl)Cl.[N+:5]([C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[N:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)([O-])=O.C(=O)(O)[O-].[Na+]>CO>[NH2:5][C:8]1[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:10][C:9]=1[N:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 23149636HCID 23149636, compound

Product 1

HCID 23149649HCID 23149649, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (1.13 ml, 13.5 mmol) and anhydrous tin dichloride (1.38 g, 7.28 mmol) were sequentially added at 0° C. to a methanol (7 ml) solution of 2-[2-nitro-4-(trifluoromethyl)phenyl]isoindoline (641 mg, 2.08 mmol), obtained as described in Referential Example 20-1. The resulting mixture was warmed to room temperature and stirred for 8.5 hours. A saturated aqueous solution of sodium bicarbonate was added to the mixture. The resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30 g, hexane/ethyl acetate=15/1). Thus, 2-[2-amino-4-(trifluoromethyl)phenyl]isoindoline (225 mg, 38.9%) was yielded as a red-orange colored oily material.

Workup

  1. customobtained
  2. extractionThe resulting mixture was extracted three times with ethyl acetate
  3. washThe obtained organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30 g, hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-3d4bc12108de42f7b652ee4149618464
Source dataset
uspto-grants-2014_08
Patent number
US08816089B2

Reaction notes

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