3-Amino-N-methylbenzamide → Ammonia

HRID 1409669Notes

Reaction equation

HRID 1409669 reaction equation
Cl[CH2:2][S:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N:12][CH:11]=[CH:10]2)(=[O:5])=[O:4].[NH2:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([NH:23][CH3:24])=[O:22]>CO>[NH3:6].[CH:13]1[C:14]2[C:9](=[CH:8][C:7]([NH:6][S:3]([CH2:2][NH:17][C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([NH:23][CH3:24])=[O:22])(=[O:5])=[O:4])=[CH:16][CH:15]=2)[CH:10]=[CH:11][N:12]=1

Participants

5

Reactant 2

HCID 6765263-Amino-N-methylbenzamideHCID 59205698HCID 59205698, compound

Product 2

HCID 222AmmoniaYield 2%HCID 59205684HCID 59205684, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 1-chloro-N-(isoquinolin-6-yl) methanesulfonamide in MeOH is added KI and the solution is heated to 60° C. for 40 minutes. The mixture is cooled to 45° C. and 3-amino-N-methylbenzamide is added and stirred at 45° C. After 2-4 hours or when TLC indicated completion of the reaction, the solvents are evaporated and the residue is taken up in EtOAc and extracted with NaHCO3 (sat). The organics are dried (Na2SO4), filtered and evaporated. Flash chromatography (SiO2, 2% NH3(2M) in MeOH/3% MeOH/CH2Cl2) gives 3-((N-isoquinolin-6-ylsulfamoyl)methylamino)-N-methylbenzamide.

Workup

  1. temperatureThe mixture is cooled to 45° C.
  2. customcompletion of the reaction
  3. customthe solvents are evaporated
  4. extractionextracted with NaHCO3 (sat)
  5. dry with materialThe organics are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-36f1eb2427e54076a8b90b712ef5f743
Source dataset
uspto-grants-2014_12
Patent number
US08921392B2

Reaction notes

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