Potassium Carbonate → HCID 68462157, compound

HRID 501178Notes

Reaction equation

HRID 501178 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[N:6][CH:5]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH2:20][NH:19][CH2:18][CH2:17]2.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH2:20][N:19]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:11])=[CH:5][N:6]=1)[CH2:18][CH2:17]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 156236,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline2×HCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 68462157HCID 68462157, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl-6-chloronicotinate (170 mg), 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (205 mg), potassium carbonate (150 mg) and dioxane (5 mL) was heated in a 100° C. oil bath overnight. An additional aliquote of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (100 mg) was added and heating was continued for five hours. The reaction was partitioned between water and EtOAc. The organics were washed with water, dried, and the solvent evaporated. The residue was purified by flash chromatography eluting with EtOAc to give methyl 6-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)nicotinate as a white solid (180 mg), m/e=329 (M+1).

Workup

  1. temperatureheating
  2. customThe reaction was partitioned between water and EtOAc
  3. washThe organics were washed with water
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was purified by flash chromatography
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-82a60c51679840a1a23d899cf1be14a6
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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