Trifluoroacetic anhydride → 6-Methoxy-3,3-dimethyl-13-nitro-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]-acridin-7-one

HRID 478690Notes

Reaction equation

HRID 478690 reaction equation
[CH3:1][C:2]1([CH3:31])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:29][CH3:30])=[CH:7][C:8]=2[NH:12][C:13]2[C:14]([C:26]([OH:28])=O)=[CH:15][C:16]3[C:21]([C:22]=2[N+:23]([O-:25])=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:3]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[CH3:30][O:29][C:6]1[CH:5]=[C:4]2[O:3][C:2]([CH3:1])([CH3:31])[CH:11]=[CH:10][C:9]2=[C:8]2[C:7]=1[C:26](=[O:28])[C:14]1[CH:15]=[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]3=[C:22]([N+:23]([O-:25])=[O:24])[C:13]=1[NH:12]2

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 220645353-[(2,2-Dimethyl-7-methoxy-2H-chromen-5-yl)amino]-4-nitro-2-naphthalene-carboxylic acid

Product 1

HCID 220645196-Methoxy-3,3-dimethyl-13-nitro-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]-acridin-7-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

772 mg of the compound obtained in Step 4 are dissolved in 45 ml of anhydrous dichloromethane, and 3 ml of trifluoroacetic anhydride are added. After stirring for 5 minutes at ambient temperature, the reaction mixture is evaporated. The residue is taken up in a mixture of dichloromethane and saturated NaHCO3 solution. After extraction of the aqueous phase with dichloromethane, the combined organic phases are treated in conventional manner and then distilled, allowing the expected product to be isolated.

Workup

  1. customthe reaction mixture is evaporated
  2. additionThe residue is taken up in a mixture of dichloromethane and saturated NaHCO3 solution
  3. extractionAfter extraction of the aqueous phase with dichloromethane
  4. additionthe combined organic phases are treated in conventional manner
  5. distillationdistilled
  6. customto be isolated

Sources & evidence

ORD record
ord-3f605cc6caf441aea8ea3a873c713991
Source dataset
uspto-grants-2003_11
Patent number
US06642248B2

Reaction notes

Loading…