Formic Acid → 1,4-Benzoxazepine-4(5H)-carboxaldehyde, 2,3-dihydro-

HRID 1861696Notes

Reaction equation

HRID 1861696 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[O:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][NH:14][CH2:13][CH2:12]1>C(OCC)(=O)C>[CH:1]([N:14]1[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:11][CH2:12][CH2:13]1)=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 218827752,3,4,5-Tetrahydro-1,4-benzoxazepine

Product 1

HCID 118195761,4-Benzoxazepine-4(5H)-carboxaldehyde, 2,3-dihydro-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (30 ml),was added dropwise to formic acid (90 ml) at room temperature and after the mixture was stirred for 30 minutes, a solution of 2,3,4,5-tetrahydro-1,4-benzoxazepine (13.0 g) in ethyl acetate (50 ml) was added dropwise at:room temperature. The mixture was then stirred for 30 minutes, after which it was diluted with ice-water and extracted with ethyl acetate. The extract was washed successively with water, aqueous solution of sodium hydroxide (NaOH/H2O), and saturated aqueous solution of sodium chloride (NaCl/H2O) and dried over anhydrous magnesium sulfate (MgSO4). The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate) to provide the title compound (14.4 g) as a viscous oil.

Workup

  1. stirringThe mixture was then stirred for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with water, aqueous solution of sodium hydroxide (NaOH/H2O), and saturated aqueous solution of sodium chloride (NaCl/H2O)
  4. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-d3e82e1467e340959e1ae268bb7035c3
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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