Formic Acid → HCID 11073927, compound

HRID 1861697Notes

Reaction equation

HRID 1861697 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][NH:13][CH2:12]1>C(OCC)(=O)C>[CH:5]([N:13]1[CH2:12][CH2:11][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14]1)=[O:7]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine

Product 1

HCID 11073927HCID 11073927, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (40 ml) was added dropwise to formic acid (80 ml) at room temperature and after the mixture was stirred for 30 minutes, a solution of 2,3,4,5-tetrahydro-1H-3-benzazepine (30 g),in ethyl acetate (80 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 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) and recrystallized from-n-hexane to provide the title compound (29 g) as colorless crystals melting at 65-66° C.

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 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)
  7. customrecrystallized from-n-hexane

Sources & evidence

ORD record
ord-f00755207374415a90e7b586d7e68586
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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