Triethylamine → methyl 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoate

HRID 2175695Notes

Reaction equation

HRID 2175695 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][C:7]([C:14]([OH:16])=O)=[CH:6]2.C(Cl)(=O)C(Cl)=O.[NH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].C(N(CC)CC)C>C(Cl)Cl.O.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][C:7]([C:14]([NH:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27])=[O:16])=[CH:6]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 65578Oxalyl chlorideHCID 103761625,6-dimethoxy-1H-indene-2-carboxylic Acid

Product 1

HCID 67087723methyl 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoateYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 5,6-dimethoxy-1H-indene-2-carboxylic acid (230 mg, 1.05 mmol) and DMF (20 μL) in DCM (10 mL) was added oxalyl chloride (267 mg, 2.10 mmol) dropwise at room temperature. The resulting mixture was stirred for 2 hours then concentrated and dried under high vacuum. The resulting acid chloride was then taken up into DCM (10 mL) and added dropwise to a stirred mixture of methyl 2-aminobenzoate (174 mg, 1.16 mmol) and triethylamine (159.1 mg, 1.58 mmol) in DCM (10 mL) 0° C. The mixture was then stirred overnight at room temperature before adding water and extracting with DCM. The organic extracts were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography with petroleum ether/ethyl acetate 5:1 (v:v) as eluent to give methyl 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoate (140 mg, 38%). LC-MS (ES-API); rt 9.35 min; m/z calculated for C20H19NO5 [M+H]+ 354.1, found 354.1.

Workup

  1. concentrationthen concentrated
  2. customdried under high vacuum
  3. stirringThe mixture was then stirred overnight at room temperature
  4. extractionextracting with DCM
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel chromatography with petroleum ether/ethyl acetate 5:1 (v:v) as eluent

Sources & evidence

ORD record
ord-9fb36a04403849ff9f143d321fe0322a
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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