Potassium Carbonate → HCID 178427653, compound

HRID 2195700Notes

Reaction equation

HRID 2195700 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([OH:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([I:15])[CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[S:22]([O:32][NH2:33])([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23]>CN(C)C=O.ClCCl>[S:22]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([O-:32])(=[O:24])=[O:23].[NH2:33][N+:3]1[C:4]2[C:9](=[CH:8][C:7]([I:15])=[CH:6][CH:5]=2)[C:10]([OH:14])=[C:11]([C:12]#[N:13])[C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10965249Amino 4-methylbenzene-1-sulfonateHCID 1785104572-Amino-3-cyano-4-hydroxy-6-iodoquinoline

Product 1

HCID 178427653HCID 178427653, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.62 g 2-amino-3-cyano-4-hydroxy-6-iodoquinoline in 10 ml of dimethylformamide is stirred with 1 g of solid potassium carbonate for 40 minutes. Then, 0.6 g O-tosylhydroxylamine in 14 ml dichloromethane is added dropwise to the reaction mixture. Stirring at room temperature is continued for 4 hours. The precipitated crystalline material is filtered off and dried to obtain 0.57 g of the title compound (MH+: 327).

Workup

  1. filtrationThe precipitated crystalline material is filtered off
  2. customdried

Sources & evidence

ORD record
ord-bb1cd1922ef3471c93f9f2b16869338f
Source dataset
uspto-grants-2012_12
Patent number
US08338411B2

Reaction notes

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