Sodium Hydroxide → 6-Iodobenzo[d][1,3]dioxol-5-amine

HRID 2189254Notes

Reaction equation

HRID 2189254 reaction equation
[I:1][C:2]1[C:3]([NH:11]C(=O)C)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[OH-].[Na+]>C(O)C.O>[I:1][C:2]1[C:3]([NH2:11])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53488067N-(6-Iodo-2H-1,3-benzodioxol-5-yl)acetamide

Product 1

HCID 534880686-Iodobenzo[d][1,3]dioxol-5-amineYield 98.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of N-(6-iodobenzo[d][1,3]dioxol-5-yl)acetamide (200 mg, 0.656 mmol) and NaOH (1.31 g, 32.8 mmol) in ethanol (26 mL) and water (6 mL) was heated to reflux with stirring for 4 h. The mixture was cooled and the solvent was removed under vacuum. The residue was partitioned between methylene chloride (100 mL) and water (100 mL). The organic layer was washed with water (2×100 mL), dried (MgSO4) and evaporated under vacuum to give 6-iodobenzo[d][1,3]dioxol-5-amine (170 mg, 98%) as orange solid. LCMS: 264 [M+1]+; 1H NMR (DMSO-d6) δ 4.88 (s, 2H), 5.87 (s, 2H), 6.47 (s, 1H), 7.07 (s, 1H).

Workup

  1. temperatureto reflux
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed under vacuum
  4. customThe residue was partitioned between methylene chloride (100 mL) and water (100 mL)
  5. washThe organic layer was washed with water (2×100 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-aa8a317752f64aa5bb52846963cf5883
Source dataset
uspto-grants-2012_12
Patent number
US08324240B2

Reaction notes

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