Triethylamine → 3-[(8-Methoxy-2,2-dimethyl-2H-chromen-5-yl)amino]-2-naphthoic acid

HRID 478693Notes

Reaction equation

HRID 478693 reaction equation
Br[C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CO[C:17]1[CH:28]=[C:27]([NH2:29])[C:20]2[CH:21]=[CH:22][C:23]([CH3:26])([CH3:25])[O:24][C:19]=2[CH:18]=1.[C:30]([O-])(=[O:32])C.[K+].C(N(CC)CC)C>CC(O)C.CC([O-])=O.CC([O-])=O.[Cu+2].O.ClCCl>[CH3:30][O:32][C:18]1[CH:17]=[CH:28][C:27]([NH:29][C:2]2[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[C:20]2[C:19]=1[O:24][C:23]([CH3:25])([CH3:26])[CH:22]=[CH:21]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 517044Potassium AcetateHCID 109981537-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamineHCID 122263533-Bromonaphthalene-2-carboxylic acid

Product 1

HCID 220645103-[(8-Methoxy-2,2-dimethyl-2H-chromen-5-yl)amino]-2-naphthoic acid

Reagents, catalysts & solvents 3

HCID 165397Cupric acetate monohydrateCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution containing 1.2 mmol of 3-bromonaphthalene-2-carboxylic acid, 1.19 mmol of 7-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamine, 2.38 mmol of potassium acetate, 10 mg of Cu(OAc)2.H2O and 1.19 mmol of triethylamine in 17 ml of 2-propanol is refluxed for 24 hours and then concentrated under reduced pressure. The residue obtained is taken up in a 2/1 mixture of dichloromethane/1N HCl. The aqueous phase is extracted with dichloromethane and the combined organic phases are then treated in conventional manner. Chromatography of the residue over silica gel (dichloromethane) allows the expected product to be isolated.

Workup

  1. temperatureis refluxed for 24 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue obtained
  4. extractionThe aqueous phase is extracted with dichloromethane
  5. additionthe combined organic phases are then treated in conventional manner
  6. customto be isolated

Sources & evidence

ORD record
ord-60cc58db8b8f4133b005747252fcd923
Source dataset
uspto-grants-2003_11
Patent number
US06642248B2

Reaction notes

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