Water → 5,6-diethoxy-7-fluoro-3H-isoindol-1-ylamine

HRID 732250Notes

Reaction equation

HRID 732250 reaction equation
C(N(CC)CC)C.S(O)(O)(=O)=O.[CH2:13]([O:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([F:28])[C:24]=1[O:25][CH2:26][CH3:27])[C:21]([NH2:29])=[N:20][CH2:19]2)[CH3:14].O>C1(C)C=CC=CC=1>[CH2:13]([O:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([F:28])[C:24]=1[O:25][CH2:26][CH3:27])[C:21]([NH2:29])=[N:20][CH2:19]2)[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 115880541H-Isoindol-3-amine, 5,6-diethoxy-4-fluoro-, sulfate (1:1)

Product 1

HCID 99917775,6-diethoxy-7-fluoro-3H-isoindol-1-ylamineYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (0.13 mL) was added to a mixture of 5,6-diethoxy-7-fluoro-2,3-dihydroisoindol-1-ylideneamine sulfate (225 mg, 0.67 mol) produced in Example 2, water (2.3 mL) and toluene (2.3 mL). The mixture was stirred at room temperature. After the layers were separated, the organic layer was re-extracted with water (1.2 mL), the aqueous layers were combined, and a 5N aqueous solution of sodium hydroxide (0.3 mL) was added thereto on ice. The mixture was stirred on ice, and then precipitated crystals were filtered and dried at room temperature under reduced pressure to give 133 mg of the title compound (yield: 84%) as grayish white crystals.

Workup

  1. customAfter the layers were separated
  2. extractionthe organic layer was re-extracted with water (1.2 mL)
  3. additiona 5N aqueous solution of sodium hydroxide (0.3 mL) was added
  4. stirringThe mixture was stirred on ice
  5. customprecipitated crystals
  6. filtrationwere filtered
  7. customdried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-83d527ff88a74737b8585138ebd9513c
Source dataset
uspto-grants-2009_09
Patent number
US07585982B2

Reaction notes

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