Formic Acid → HCID 10080884, compound

HRID 1861698Notes

Reaction equation

HRID 1861698 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[CH2:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14][CH2:13][NH:12]1>C(OCC)(=O)C>[CH:5]([N:12]1[CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:11]1)=[O:7]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 104644722,3,4,5-Tetrahydro-1H-benzo[c]azepine

Product 1

HCID 10080884HCID 10080884, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (20 ml) was added dropwise to formic acid (60 ml) at room temperature and after the mixture was stirred for 30 minutes, a solution of 2,3,4,5-tetrahydro 1H-2-benzazepine (10.71 g, 72.75 mmol) in ethyl acetate (5 ml) was added dropwise at room temperature. This mixture was stirred for 3 hours, after which it was diluted with ice-water and extracted with ethyl acetate. The extract was washed successively with water, aqueous solution of potassium carbonate (K2CO3), and saturated NaCl/H2O and dried over 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 (11.35 g) as colorless oil.

Workup

  1. stirringThis mixture was stirred for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with water, aqueous solution of potassium carbonate (K2CO3), and saturated NaCl/H2O
  4. dry with materialdried over 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-3dc758339f814a6baef4e20b32934c81
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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