Water → HCID 23505619, compound

HRID 1884367Notes

Reaction equation

HRID 1884367 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9](N)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[C:12]([O:15]C(=O)C)(=O)[CH3:13].O.[N:20]1C=CC=CC=1>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:13][C:12]([NH2:20])=[O:15])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 891481,4-Benzodioxan-6-ylamine

Product 1

HCID 23505619HCID 23505619, compoundYield 71%

Procedure

To a solution of 1,4-benzodioxan-6-amine (2.0 g, 13.2 mmol) in 5 mL of anhydrous pyridine at 0° C. was added acetic anhydride (1.87 mL, 19.9 mmol) and the solution was stirred at rt overnight. The solution was then added to 50 mL of water and was extracted with 2×50 mL of EtOAc. The extract was washed with 1N HCl, water and brine, then dried over MgSO2 and concentrated in vacuo to yield the title compound (1.82 g, 71%). 1H NMR (CDCl3): 7.13 (m, 2H), 6.88 (dd, 1H), 6.80 (d, 1H), 4.25 (s, 4H), 2.15 (s, 3H).

Workup

  1. extractionwas extracted with 2×50 mL of EtOAc
  2. washThe extract was washed with 1N HCl, water and brine
  3. dry with materialdried over MgSO2
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba1ded362b3e4649ac75e91db1251795
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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