Iodine → 2,2,4-Trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one

HRID 909287Notes

Reaction equation

HRID 909287 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[O:8][C:7](=[O:15])[C:6]=2[CH:16]=1.II>CC(C)=O>[CH3:6][C:5]1([CH3:14])[CH:4]=[C:3]([CH3:2])[C:16]2[C:2](=[CH:3][CH:4]=[C:5]3[C:6]=2[C:7](=[O:15])[O:8][C:9]2[C:14]3=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:1]1

Participants

4

Reactant 2

HCID 807IodineHCID 233789368-Aminobenzo[c]chromen-6-one

Product 1

HCID 104937872,2,4-Trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-oneYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
105 °C

Procedure

In a pressure tube, 8-aminobenzo[c]chromen-6-one (Reference Compound No. 1-1-(2), 8.81 g, 41.7 mmol) was dissolved in acetone (300 mL), then iodine (4.24 g, 16.7 mmol) was added thereto, then the pressure tube was sealed, and then the reaction mixture was stirred at 105° C. for 2 days. After cooling down, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (4.83 g) as a yellow solid. (Yield 40%)

Workup

  1. customthe pressure tube was sealed
  2. temperatureAfter cooling down
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b3bac010d39f40aa8bf54a1f1eeb7257
Source dataset
uspto-grants-2011_09
Patent number
US08017775B2

Reaction notes

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