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

HRID 1476727Notes

Reaction equation

HRID 1476727 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-8b74519ed7674fdcb4087268b86d389e
Source dataset
uspto-grants-2016_08
Patent number
US09402832B2

Reaction notes

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