Triethylamine → Methyl 2-(6,7-dimethoxy-1,2-dihydronaphthalene-3-carboxamido)benzoate

HRID 2175708Notes

Reaction equation

HRID 2175708 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CCN(CC)CC.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[CH:27]=[C:26]([C:33](Cl)=[O:34])[CH2:25][CH2:24]2>C(Cl)Cl>[CH3:32][O:31][C:30]1[CH:29]=[C:28]2[C:23](=[CH:22][C:21]=1[O:20][CH3:19])[CH2:24][CH2:25][C:26]([C:33]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:34])=[CH:27]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 103548826,7-dimethoxy-3,4-dihydronaphthalene-2-carbonyl Chloride

Product 1

HCID 67087821Methyl 2-(6,7-dimethoxy-1,2-dihydronaphthalene-3-carboxamido)benzoateYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxylic acid (476 mg, 2 mmol) and SOCl2 (1.5 mL, 20 mmol) in toluene (20 mL) was heated at 50° C. for 1 hour. The solvent was then removed under reduced pressure to give 6,7-dimethoxy-3,4-dihydronaphthalene-2-carbonyl chloride which was used directly in the next step without further purification. To a stirred solution of methyl 2-aminobenzoate (332 mg, 2.2 mmol) and Et3N (0.8 mL, 6 mmol) in anhydrous DCM (20 mL) was added 6,7-dimethoxy-3,4-dihydronaphthalene-2-carbonyl chloride in anhydrous DCM (2 mL) dropwise at 0° C. The resulting mixture was stirred at room temperature overnight. The reaction was quenched with water and extracted with DCM. The combined organic phase was dried over sodium sulfate, the solvent was removed under reduced pressure and the residue was purified by flash column, eluting with petroleum ether/ethyl acetate (10:1) to give methyl 2-(6,7-dimethoxy-1,2-dihydronaphthalene-3-carboxamido)benzoate (330 mg, 45%). LC-MS (ES-API); rt 9.27 min; m/z calculated for C21H21NO5 [M+Na]+ 390.1, found 390.1.

Workup

  1. customwas used directly in the next step without further purification
  2. customThe reaction was quenched with water
  3. extractionextracted with DCM
  4. dry with materialThe combined organic phase was dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customthe residue was purified by flash column
  7. washeluting with petroleum ether/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-8cb4196919a3427590018dfde6738cb6
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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