N,N-Dimethylethylenediamine → 1-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid (2-dimethylamino-ethyl)-amide

HRID 1406136Notes

Reaction equation

HRID 1406136 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([Cl:19])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])CCC.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH2:24]>C(O)C>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH:24][C:6]([C:8]1[N:9]=[C:10]([Cl:19])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 860145021-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 112778171-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid (2-dimethylamino-ethyl)-amideYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 28 mg (0.1 mmol) of 1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester from example A-1 c), 116 μl (1 mmol) of N,N-dimethyl-ethane-1,2-diamine and 0.5 ml of absolute ethanol was stirred at ambient temperature for 18 h. Then the solvent was evaporated in vacuo, the residue suspended in 5 ml of water, and mixture was extracted with 2×35 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated in vacuo to give a yellowish solid. 29 mg of the title compound were obtained; MS-(+)-ion: M+1=294.1.

Workup

  1. customThen the solvent was evaporated in vacuo
  2. extractionmixture was extracted with 2×35 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customto give a yellowish solid

Sources & evidence

ORD record
ord-987391bf32aa41c289f95f66631c6cb3
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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