Potassium Carbonate → 1-Dimethylaminomethyl-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester

HRID 908874Notes

Reaction equation

HRID 908874 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[I-].C[CH:28]=[N+:29]=[CH:30]C.[C:32]([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:28][N:29]([CH3:30])[CH3:32])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21892197N,N-dimethylmethyleneammoniumiodideHCID 667130924-Hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 667131731-Dimethylaminomethyl-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl esterYield 16.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-Hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (177 mg, 0.5 mmol; see example D-1f), N,N-dimethylmethyleneammonium iodide (94 mg, 0.5 mmol), K2CO3 (104 mg, 0.75 mmol), and anhydrous CH2Cl2 (3 ml) was stirred at ambient temperature for 2.5 d before the mixture was concentrated in vacuo. To the residue was added water (15 ml), the mixture was acidified by addition of 6 N HCl and then washed with Et2O (3×30 ml). Subsequently, the mixture was neutralized by the addition of concentrated aqueous NaHCO3 and extracted with EtOAc (20 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a dark oil (34 mg); MS-(+)-ion M+1=411.1.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionTo the residue was added water (15 ml)
  3. additionthe mixture was acidified by addition of 6 N HCl
  4. washwashed with Et2O (3×30 ml)
  5. additionSubsequently, the mixture was neutralized by the addition of concentrated aqueous NaHCO3
  6. extractionextracted with EtOAc (20 ml)
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-271c227d81004d9f9de6f2ef1e5cb72c
Source dataset
uspto-grants-2011_09
Patent number
US08017625B2

Reaction notes

Loading…