Ammonia → Ethyl 3-phenyl-1-isoquinolinepropanoate

HRID 2232510Notes

Reaction equation

HRID 2232510 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.O.N.[CH2:29](O)[CH3:30]>>[C:1]1([C:7]2[N:8]=[C:9]([CH2:17][CH2:18][C:19]([O:21][CH2:29][CH3:30])=[O:20])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 13769242HCID 13769242, compound

Product 1

HCID 13769243Ethyl 3-phenyl-1-isoquinolinepropanoate

Procedure

3-Phenyl-1-isoquinolinepropanoic acid (6.7 g) and concentrated sulphuric acid (7 cc) in ethanol (0 cc) are stirred for 20 hours at 20° C. The solution is poured into water (400 cc) and the aqueous phase alkalinised with concentrated ammonia solution. The mixture is extracted with methylene chloride (3×100 cc), and the organic phase dried and evaporated to dryness under reduced pressure. Ethyl 3-phenyl-1-isoquinolinepropionate (6.3 g), m.p. 60° C., is obtained.

Workup

  1. extractionThe mixture is extracted with methylene chloride (3×100 cc)
  2. customthe organic phase dried
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b820ab9aa3494b5f9f92726ab5b56d8a
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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