N-methyl-2-pyrrolidone → HCID 22175258, compound

HRID 1797679Notes

Reaction equation

HRID 1797679 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:5](=[O:20])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9](Br)=[CH:8][CH:7]=2.[CH3:25][N:26]1CCCC1=O.[Cl-].[NH4+]>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[NH2:1][CH2:2][C:3]1[N:4]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:5](=[O:20])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([C:25]#[N:26])=[CH:8][CH:7]=2

Participants

7

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 25517Ammonium ChlorideHCID 22175497HCID 22175497, compound

Product 1

HCID 22175258HCID 22175258, compoundYield 74.5%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of 3-(aminomethyl)-6-bromo-2-isobutyl-4-phenylisoquinolin-1(2H)-one (15.0 g), zinc cyanide (2.74 g), tetrakis(triphenylphosphine)palladium (1.35 g), N-methylpyrrolidone (75 ml) and water (0.75 ml), was stirred under a nitrogen atmosphere at an inner temperature of 54–56° C. To the reaction mixture was added dropwise saturated aqueous ammonium chloride-25% ammonium hydroxide-water (4:1:4, 37.5 ml) over 30 min at the same temperature, and the mixture was stirred for 1 h and below 5° C. for 1 h. The obtained crystals were collected by filtration and suspended in acetonitrile (105 ml). The suspension was dissolved at 80° C. To the obtained solution was added activated carbon (0.75 g) and the mixture was stirred for 10 min. The activated carbon was filtered off and washed with acetonitrile (15 ml). The filtrate was combined and cooled to 25° C. to give crystals. Water (120 ml) was added dropwise and the obtained mixture was cooled to 5° C. and stirred for 1 h. The obtained crystals were collected by filtration to give the title compound (9.6 g, yield 74.5%).

Workup

  1. stirringthe mixture was stirred for 1 h and below 5° C. for 1 h
  2. filtrationThe obtained crystals were collected by filtration
  3. dissolutionThe suspension was dissolved at 80° C
  4. additionTo the obtained solution was added activated carbon (0.75 g)
  5. stirringthe mixture was stirred for 10 min
  6. filtrationThe activated carbon was filtered off
  7. washwashed with acetonitrile (15 ml)
  8. customto give crystals
  9. temperaturethe obtained mixture was cooled to 5° C.
  10. stirringstirred for 1 h
  11. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-84f441a5e3e8475793626c4dad4c4be9
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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