Isopropanol → 3-[(2,2-Dimethyl-7-methoxy-2H-chromen-5-yl)amino]-4-nitro-2-naphthalene-carboxylic acid

HRID 1827905Notes

Reaction equation

HRID 1827905 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:15])([CH3:14])[O:7]2.Cl[C:17]1[C:18]([C:30]([OH:32])=[O:31])=[CH:19][C:20]2[C:25]([C:26]=1[N+:27]([O-:29])=[O:28])=[CH:24][CH:23]=[CH:22][CH:21]=2.C([O-])(=O)C.[K+].CC(O)C>CC([O-])=O.CC([O-])=O.[Cu+2].O.C(N(CC)CC)C>[CH3:14][C:6]1([CH3:15])[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:2]=2[NH:1][C:17]2[C:18]([C:30]([OH:32])=[O:31])=[CH:19][C:20]3[C:25]([C:26]=2[N+:27]([O-:29])=[O:28])=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:7]1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 517044Potassium AcetateHCID 109981537-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamineHCID 220645163-Chloro-4-nitro-2-naphthalenecarboxylic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 8471TriethylamineSolvent

Procedure

To 3.3 g of 5-amino-7-methoxy-2,2-dimethylchromene there are added 3 g of the compound obtained in Step 3 above, 3.4 g of potassium acetate, 375 mg of Cu(OAc)2.H2O and 120 ml of 2-propanol containing 3.8 ml of triethylamine. The solution is refluxed for 5 days and is then evaporated under reduced pressure. The residue is taken up in a 1/1 mixture of dichloromethane and 1N aqueous HCl solution. After extraction of the aqueous phase, the combined organic phases are treated in customary manner. Chromatography over silica gel (dichloromethane/methanol: gradient from 0.1 to 1%) allows the expected product to be isolated.

Workup

  1. temperatureThe solution is refluxed for 5 days
  2. customis then evaporated under reduced pressure
  3. additionThe residue is taken up in a 1/1 mixture of dichloromethane and 1N aqueous HCl solution
  4. extractionAfter extraction of the aqueous phase
  5. additionthe combined organic phases are treated in customary manner
  6. customto be isolated

Sources & evidence

ORD record
ord-9d7284813ea94002b68a168684045396
Source dataset
uspto-grants-2006_06
Patent number
US07056929B2

Reaction notes

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