Water → Ethyl 2-(1,2,3,4-tetrahydroisoquinolin-2-yl)nicotinate

HRID 1018466Notes

Reaction equation

HRID 1018466 reaction equation
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[CH2:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][NH:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][N:15]1[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27347171,2,3,4-Tetrahydroisoquinoline HydrochlorideHCID 2796614Ethyl chloronicotinate

Product 1

HCID 18401743Ethyl 2-(1,2,3,4-tetrahydroisoquinolin-2-yl)nicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.0 g (19.4 mmol) of ethyl 2-chloronicotinate, together with 3.2 g (19.4 mmol) of 1,2,3,4-tetrahydroisoquinoline hydrochloride and 5.36 g of potassium carbonate were heated at 110° C. for 3 h in 50 ml of DMF while stirring. Water was then added and the whole was extracted with ether; the ether phase was then washed with ammonium chloride, dried and evaporated. The crude product was purified chromatographically (silica gel/heptane-ethyl acetate 20-1), giving a yield of 4.8 g (87%).

Workup

  1. extractionthe whole was extracted with ether
  2. washthe ether phase was then washed with ammonium chloride
  3. customdried
  4. customevaporated
  5. customThe crude product was purified chromatographically (silica gel/heptane-ethyl acetate 20-1)
  6. customgiving a yield of 4.8 g (87%)

Sources & evidence

ORD record
ord-eb315b9e43ae48e9a7d087ed41eb5751
Source dataset
uspto-grants-2002_11
Patent number
US06482832B1

Reaction notes

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