Triethylamine → 5,6-dihydro-5-oxo-11H-indeno [1,2-c]isoquinoline

HRID 967728Notes

Reaction equation

HRID 967728 reaction equation
[C:1]1(=O)O[C:5](=[O:6])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[C:13]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1CBr)#[N:14].C(N(CC)CC)C>C(#N)C>[O:6]=[C:5]1[C:4]2[C:3](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]2[CH2:1][C:16]3[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=3[C:13]=2[NH:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12801Homophthalic anhydrideHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 101053885,6-dihydro-5-oxo-11H-indeno [1,2-c]isoquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of homophthalic anhydride (324 mg, 2.0 mmol) in acetonitrile (15 mL) was added 2-cyanobenzyl bromide (431 mg, 2.0 mmol, 1.0 eq) and triethylamine (5 mL). The reaction was stirred under inert atmosphere at room temperature for 30 minutes, after which time a yellow precipitate appeared. The reaction mixture was then heated at reflux for 18 h and the resulting white precipitate was filtered, washed using acetonitrile (3×8 mL) and dried under vacuum to provide Compound 13a as a white crystalline solid. Yield=150 mg (32%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 18 h
  3. filtrationthe resulting white precipitate was filtered
  4. washwashed
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8c9830ebd5bf43b5b84b086fcbd83943
Source dataset
uspto-grants-2005_10
Patent number
US06956035B2

Reaction notes

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