Isoquinoline-1-carboxylic acid → N-methoxy-N-methylisoquinoline-1-carboxamide

HRID 2111903Notes

Reaction equation

HRID 2111903 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([C:23]([OH:25])=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1.Cl.[CH3:27][NH:28][O:29][CH3:30]>ClCCl>[CH3:27][N:28]([O:29][CH3:30])[C:23]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1)=[O:25]

Participants

5

Reactant 3

HCID 68092Isoquinoline-1-carboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 58678647N-methoxy-N-methylisoquinoline-1-carboxamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Portions of 1,1′-carbonyldiimidazole (2.06 g, 12.7 mmol) are added to a stirred mixture of isoquinoline-1-carboxylic acid (2.00 g, 11.6 mmol) in dichloromethane (25 ml). N,O-dimethylhydroxylamine hydrochloride (1.24 g, 12.7 mmol) is added and the mixture is stirred at ambient temperature overnight. The reaction mixture is diluted with dichloromethane and then washed with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. The organic solution is dried with sodium sulfate, filtered, and concentrated to give 2.5 g of N-methyl N-methoxy isoquinoline-1-carboxamide, which is used in the next step without further purification: mass spectrum (ion spray): m/z=217.0 (M+1).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialThe organic solution is dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7809da0feeb436baab27a1f3d649c8d
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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