3-Amino-N-methylbenzamide → Ammonia

HRID 1409668Notes

Reaction equation

HRID 1409668 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:7]([Cl:16])=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[N:11][CH:10]=[CH:9]2)=[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>[NH3:5].[Cl:16][C:7]1[C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:17][C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([NH:23][CH3:24])=[O:22])=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2

Participants

5

Reactant 2

HCID 6765263-Amino-N-methylbenzamideHCID 59205709HCID 59205709, compound

Product 2

HCID 222AmmoniaHCID 59205736HCID 59205736, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 2-chloro-N-(5-chloroisoquinolin-6-yl) acetamide 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 indicates 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, NH3(2M) in MeOH/3% MeOH/CH2Cl2) gives pure 3-(2-(5-chloroisoquinolin-6-ylamino)-2-oxoethylamino)-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-e63580e1136e4de484113b892ffdc796
Source dataset
uspto-grants-2014_12
Patent number
US08921392B2

Reaction notes

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