Dichloromethane → 1,2,3,4-Tetrahydro-6-hydroxy-7-methoxy-2-propionyl-isoquinoline

HRID 597204Notes

Reaction equation

HRID 597204 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].Cl.[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[CH2:14][NH:13][CH2:12][CH2:11]2.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O>[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[CH2:14][N:13]([C:1](=[O:4])[CH2:2][CH3:3])[CH2:12][CH2:11]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 62324Propionyl chlorideHCID 241893971,2,3,4-Tetrahydro-6-hydroxy-7-methoxy-isoquinoline-hydrochloride

Product 1

HCID 214470131,2,3,4-Tetrahydro-6-hydroxy-7-methoxy-2-propionyl-isoquinolineYield 69.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

55.5 g of propionyl chloride are added dropwise at room temperature over a period of one hour to a mixture of 86.3 g of 1,2,3,4-tetrahydro-6-hydroxy-7-methoxy-isoquinoline-hydrochloride, 138,2 g of potassium carbonate, 600 ml of methylene chloride, and 480 ml of water. The mixture is stirred for an additional 18 hours, the organic phase is separated, and the aqueous phase is extracted twice with methylene chloride. The methylene chloride extracts are dried and evaporated. 65.8 g of 1,2,3,4-tetrahydro-6-hydroxy-7-methoxy-2-propionyl-isoquinoline are obtained. m.p. = 116° - 118° C. (ethyl acetate - diisopropyl ether).

Workup

  1. customthe organic phase is separated
  2. extractionthe aqueous phase is extracted twice with methylene chloride
  3. dry with materialThe methylene chloride extracts are dried
  4. customevaporated

Sources & evidence

ORD record
ord-ddd7d265e0c144028128f0ea2938ee32
Source dataset
uspto-grants-1977_03
Patent number
US04013663

Reaction notes

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