Serinol → HCID 11245187, compound

HRID 523725Notes

Reaction equation

HRID 523725 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([Cl:23])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:24][CH:25]([CH2:28][OH:29])[CH2:26][OH:27]>C(O)C>[OH:27][CH2:26][CH:25]([NH:24][C:6]([C:8]1[N:9]=[C:10]([Cl:23])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH:20]([CH3:21])[CH3:22])=[CH:13][CH:12]=2)=[O:7])[CH2:28][OH:29]

Participants

4

Reactant 2

HCID 68294SerinolHCID 18698144HCID 18698144, compound

Product 1

HCID 11245187HCID 11245187, compoundYield 114.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.035 gm of 1-chloro-4-hydroxy-6-isopropoxy-isoquinoline-3-carboxylic acid butyl ester and 0.088 g of 2-amino-propane-1,3-diol were dissolved in 1 ml of ethanol and the mixture was refluxed for 24 h. The reaction mixture was concentrated and the residue was dissolved in 10 ml of ethyl acetate. The ethyl acetate solution was extracted with 5 ml of aqueous 1M HCl and water, dried (sodium sulfate) and concentrated to give 0.042 g of a white solid: MS-(+)-ion: 355.1.

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in 10 ml of ethyl acetate
  4. extractionThe ethyl acetate solution was extracted with 5 ml of aqueous 1M HCl and water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cb1b46dee7bf4415aa70874404f52b30
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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