Toluene → 8,9,10,11-tetrahydroazepino[1,2-b]isoquinolin-5(7H)-one

HRID 369959Notes

Reaction equation

HRID 369959 reaction equation
[C:1]1(=O)[O:7][C:5](=O)[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[NH2:13]OC1CCCCCC=1.[C:22]1(C)C=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[CH:11]1[CH:10]=[CH:9][CH:8]=[C:4]2[C:3]=1[CH:2]=[C:1]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:13]1[C:5]2=[O:7]

Participants

5

Reactant 3

HCID 1140TolueneHCID 12801Homophthalic anhydrideHCID 18353297HCID 18353297, compound

Product 1

HCID 127306378,9,10,11-tetrahydroazepino[1,2-b]isoquinolin-5(7H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Homophthalic anhydride (4.86 g, 30 mmol) was added portionwise over 10 minutes to a refluxing solution of 1-aza-2-methoxycycloheptene (4.20 g, 33 mmol) in toluene. After addition was complete, the reaction mixture was heated an additional 1 h before cooling to ambient temperature. The reaction mixture was diluted with chloroform, the resulting solution was washed twice with sodium hydroxide, and the dried (magnesium sulfate) organic layer was concentrated in vacuo. The residue was chromatographed on silica gel using chloroform, followed by 4% methanol in chloroform, as eluent to give the desired compound. This was triturated with 20% ether in hexanes (40 ml) to yield the title compound as an off-white solid (2.21 g, 42%), m.p. 99-101° C.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was heated an additional 1 h
  3. washthe resulting solution was washed twice with sodium hydroxide
  4. dry with materialthe dried (magnesium sulfate) organic layer
  5. concentrationwas concentrated in vacuo
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-37eb64fedb1b474a8dc1525c763a2745
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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