Triethylamine → 8-Methoxy-6H-11-oxa-6-aza-benzo[a]fluoren-5-one

HRID 967729Notes

Reaction equation

HRID 967729 reaction equation
Br[C:2](C)([C:6]1[C:7](=[C:11](C)[CH:12]=[CH:13][CH:14]=1)[C:8]([O-])=[O:9])C([O-])=O.[OH:17][C:18]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:19]=1[C:20]#[N:21].C(N(CC)CC)C>C(#N)C.C(=O)(O)[O-].[Na+]>[CH3:27][O:26][C:23]1[CH:22]=[C:19]2[C:18](=[CH:25][CH:24]=1)[O:17][C:2]1[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[C:8](=[O:9])[NH:21][C:20]2=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70225292-Hydroxy-5-methoxybenzonitrileHCID 131725194alpha-Bromodimethylhomophthalate

Product 1

HCID 116375298-Methoxy-6H-11-oxa-6-aza-benzo[a]fluoren-5-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

α-Bromodimethylhomophthalate (20a) (1.16 g) and 2-hydroxy-5-methoxy-benzonitrile (0.6 g, 4 mmol, 1 eq) were dissolved by warming in acetonitrile (6 mL). Triethylamine (5.6 mL, 10 eq) was then added and the reaction was heated at reflux for 48 h under inert atmosphere, then cooled to room temperature. The reaction mixture was diluted with saturated sodium bicarbonate (40 mL) and the resulting suspension was allowed to stir for 2 h, and was then filtered. The filtercake was washed sequentially with 1 N HCl (2×50 mL), acetonitrile (2×50 mL) and dichloromethane (50 mL), then dried in a vacuum oven at 50° C. for three days to provide Compound 22a as an white solid. Yield=0.81 g (76%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 48 h under inert atmosphere
  3. filtrationwas then filtered
  4. washThe filtercake was washed sequentially with 1 N HCl (2×50 mL), acetonitrile (2×50 mL) and dichloromethane (50 mL)
  5. customdried in a vacuum oven at 50° C. for three days

Sources & evidence

ORD record
ord-0784b5b5b0464a1b9470530301fef300
Source dataset
uspto-grants-2005_10
Patent number
US06956035B2

Reaction notes

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