Acetic Anhydride → HCID 21276160, compound

HRID 1381503Notes

Reaction equation

HRID 1381503 reaction equation
[CH:1]1[NH:2][CH:3]=[CH:4][C:5]2[C:6]=1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2.[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:15][C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]2[C:5]=1[CH:4]=[CH:3][NH:2][CH:1]=2)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 21276156HCID 21276156, compound

Product 1

HCID 21276160HCID 21276160, compound

Procedure

Cyclohepta[1,2-c]pyridine, N-oxide (24.00 g, 0.147 mole) was added portionwise to a stirred solution of acetic anhydride (140 ml). The resulting yellow mixture was then stirred for 2 hours at its reflux temperature and overnight at room temperature. Excess acetic anhydride was removed by evaporation at ~55° C. on a rotary evaporator and the dark brown, oily residue was distilled (170°, 0.03 mm) and chromatographed on silica gel eluting with a mixture of ethyl acetate in methylene chloride (1:4) to give the desired product.

Workup

  1. customExcess acetic anhydride was removed by evaporation at ~55° C. on a rotary evaporator
  2. distillationthe dark brown, oily residue was distilled (170°, 0.03 mm)
  3. customchromatographed on silica gel eluting with a mixture of ethyl acetate in methylene chloride (1:4)

Sources & evidence

ORD record
ord-1bdd40be5e674f7db52ca7111d5dd5cf
Source dataset
uspto-grants-1989_02
Patent number
US04803210

Reaction notes

Loading…