7-Fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine → 7-Fluoro-2,3-dihydro-1,4-benzodioxin-5-amine

HRID 1054445Notes

Reaction equation

HRID 1054445 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1

Participants

4

Reactant 1

HCID 688171507-Fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine

Product 1

HCID 666806007-Fluoro-2,3-dihydro-1,4-benzodioxin-5-amineYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (400 mg) was added to a solution of 7-fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine (2.0 g, 10 mmol) in methanol (50 mL) and stirring was continued at 25° C. under H2 atmosphere for 3 h. The reaction mixture was filtered over celite bed and washed with methanol. The filtrate and the washings were concentrated under reduced pressure to afford 7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-amine (Int-27) (1.6 g, 94% yield) as pale brown liquid. MS (ESI): m/z 170.1 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered over celite bed
  2. washwashed with methanol
  3. concentrationThe filtrate and the washings were concentrated under reduced pressure

Sources & evidence

ORD record
ord-2805175b2ab04a77a47af2a8f80b62cb
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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