3-Amino-N-methylbenzamide → Ammonia

HRID 1253863Notes

Reaction equation

HRID 1253863 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-0393f6c9ca7f4f0a9b1be855693bb32f
Source dataset
uspto-grants-2013_06
Patent number
US08455513B2

Reaction notes

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