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

HRID 1633529Notes

Reaction equation

HRID 1633529 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH3:14])([CH3:13])[O:10]2)=[C:5]([NH:15][C:16]2[C:17]([C:26](O)=[O:27])=[CH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[O:10][C:9]([CH3:14])([CH3:13])[CH:8]=[CH:7][C:6]2=[C:5]2[C:4]=1[C:26](=[O:27])[C:17]1[CH:18]=[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]3=[CH:25][C:16]=1[NH:15]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 186796173-[(7-Methoxy-2,2-dimethyl-2H-chromen-5-yl)amino]-2-naphthoic acid

Product 1

HCID 220645146-Methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.02 mmol of the compound obtained in Step A in 14 ml of dichloromethane is treated with 1 ml of trifluoroacetic acid. After 2 hours at room temperature, the reaction mixture is evaporated. The residue is taken up in a mixture of dichloromethane and a saturated NaHCO3 solution, extracted with dichloromethane, washed with a 10% sodium hydroxide solution and then extracted again with dichloromethane. After conventional treatment, chromatography of the residue over silica gel (dichloromethane/methanol: 98/2) enables isolation of the expected product.

Workup

  1. customthe reaction mixture is evaporated
  2. additionThe residue is taken up in a mixture of dichloromethane
  3. extractiona saturated NaHCO3 solution, extracted with dichloromethane
  4. washwashed with a 10% sodium hydroxide solution
  5. extractionextracted again with dichloromethane

Sources & evidence

ORD record
ord-1aa9335144ed4df99039e2b1c437b8c6
Source dataset
uspto-grants-2003_01
Patent number
US06503919B1

Reaction notes

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