Ammonia → HCID 21283634, compound

HRID 2232506Notes

Reaction equation

HRID 2232506 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.N.[CH2:28](O)[CH3:29]>O>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH2:17][CH2:18][C:19]([O:21][CH2:28][CH3:29])=[O:20])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 1118Sulfuric AcidHCID 13769240HCID 13769240, compound

Product 1

HCID 21283634HCID 21283634, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Phenyl-3-isoquinolinepropanoic acid (2 g) and concentrated sulphuric acid (2 cc) in absolute ethanol (20 cc) are stirred for 20 hours at room temperature (approximately 20° C.). The mixture is diluted with water (100 cc), alkalinised to pH 9 with concentrated ammonia solution and extracted with methylene chloride (3×50 cc). The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure. Ethyl 1-phenyl-3-isoquinolinepropionate (1.9 g) is obtained in the form of an oil, the proton NMR spectrum of which, in deuterated chloroform, has the following characteristics:

Workup

  1. extractionextracted with methylene chloride (3×50 cc)
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-178ba0a2ffe447d9a0c5ba177a4dbb1f
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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