Tetrahydrofuran → (2-Fluoro-4-nitrophenyl)methanamine

HRID 1428785Notes

Reaction equation

HRID 1428785 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.O1CCCC1>>[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[CH2:4][NH2:5]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 708476692-(2-Fluoro-4-nitrobenzyl)isoindoline-1,3-dione

Product 1

HCID 45121148(2-Fluoro-4-nitrophenyl)methanamineYield 41.5%

Procedure

To a solution of 2-(2-fluoro-4-nitrobenzyl)isoindoline-1,3-dione (1.35 g, 4.48 mmol) in tetrahydrofurane 65% hydrazine monohydrate (1.3 mL, 4 eq) was added. The mixture was refluxed for 6 h. After the starting material was consumed, the mixture was cooled down to room temperature and treated with potassium bicarbonate to pH 12˜13. Then it was extracted with ethyl acetate and washed with brine. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave (2-fluoro-4-nitrophenyl)methanamine (316 mg, 41%).

Workup

  1. temperatureThe mixture was refluxed for 6 h
  2. customAfter the starting material was consumed
  3. additiontreated with potassium bicarbonate to pH 12˜13
  4. extractionThen it was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Sources & evidence

ORD record
ord-6743afb4006145d99b249d262d228b6e
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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