Water → HCID 69522199, compound

HRID 1181429

Reaction equation

HRID 1181429 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]=[C:15]2[C:20]([OH:22])=[O:21])([O-:9])=[O:8].IC.O>CN(C)C=O>[N+:7]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]=[C:15]2[C:20]([O:22][CH3:1])=[O:21])([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2856465-Nitroisoquinoline-1-carboxylic acid

Product 1

HCID 69522199HCID 69522199, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (23 g, 167 mmol) was added to a solution of 5-nitro-isoquinoline-1-carboxylic acid (Description 104, 2.7 g, 12.4 mmol) in N,N-dimethylformamide (50 ml) at room temperature. Iodomethane (1.0 ml, 16.1 mmol) was then added and the reaction stirred at room temperature for 20 h. Water (300 ml) was added and the mixture was extracted with ethyl acetate (2×200 ml). The combined organic phases were washed with water (2×100 ml), brine (100 ml) then dried (Na2SO4) and evaporated. Purification of the residue by column chromatography eluting with ethyl acetate-isohexane (7:13 increasing to 1:1) gave the title compound (558 mg, 19%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×200 ml)
  2. washThe combined organic phases were washed with water (2×100 ml), brine (100 ml)
  3. dry with materialthen dried (Na2SO4)
  4. customevaporated
  5. customPurification of the residue by column chromatography
  6. washeluting with ethyl acetate-isohexane (7:13 increasing to 1:1)

Sources & evidence

ORD record
ord-414e8a5c44594230bd4f03687af284a8
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Linked notes

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