Water → HCID 131729961, compound

HRID 2390022Notes

Reaction equation

HRID 2390022 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11](O)=O)[N:2]=1.Cl.CN[O:17][CH3:18].C[CH2:20][N:21]=[C:22]=NCCCN(C)C.C(N(CC)CC)C.[OH2:37]>ClCCl>[CH3:18][O:17][N:21]([CH3:22])[C:20]([CH2:11][C:3]1[N:2]=[CH:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:37]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 124656Isoquinoline-3-carboxylic acid

Product 1

HCID 131729961HCID 131729961, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg of 3-isoquinolinecarboxylic acid, 169 mg of N,O-dimethylhydroxylamine monohydrochloride, 332 mg of WSC, and 582 mg of triethylamine were dissolved in 2 mL of dichloromethane, followed by stirring at room temperature for 3 hours. Water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (chloroform alone) to obtain 169 mg (yield 67%) of a title compound as a pale yellow solidified product.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was then washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified

Sources & evidence

ORD record
ord-dfde8214cdce47d99158e7bc81e4cdbc
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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