N-(2-aminoethyl)acetamide → 1-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid (2-acetylamino-ethyl)-amide

HRID 1866322Notes

Reaction equation

HRID 1866322 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.[NH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25]>C(O)C>[C:24]([NH:23][CH2:22][CH2:21][NH:20][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])(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 860145021-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 113926541-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid (2-acetylamino-ethyl)-amideYield 104%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 56 mg (0.2 mmol) of 1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester from example B-1 c), 227 mg (2 mmol) of N-(2-amino-ethyl)-acetamide and 0.8 ml of absolute ethanol was stirred at ambient temperature for 3 days. Then the solvent was evaporated in vacuo, the residue suspended in 3 ml of water, and the pH of the mixture was adjusted 2 to 3 by the addition of aqueous IN HCl. The mixture was extracted with 2×25 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated in vacuo to give a yellowish solid. 64 mg of the title compound were obtained; MS-(+)-ion: M+1=308.1.

Workup

  1. customThen the solvent was evaporated in vacuo
  2. additionby the addition of aqueous IN HCl
  3. extractionThe mixture was extracted with 2×25 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give a yellowish solid

Sources & evidence

ORD record
ord-d4646e704f4647aabdec9cefe8f74e64
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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