Ammonia → HCID 22175497, compound

HRID 1797499Notes

Reaction equation

HRID 1797499 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([CH2:17]Cl)=[C:5]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH3:25]>O1CCCC1.C(O)C>[NH2:25][CH2:17][C:6]1[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:8](=[O:12])[C:9]2[C:4]([C:5]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 222AmmoniaHCID 22175642HCID 22175642, compound

Product 1

HCID 22175497HCID 22175497, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 6-bromo-3-chloromethyl-2-isobutyl-4-phenyl-1(2H)-isoquinolinone (10 g, 24.7 mmol) in tetrahydrofuran (20 mL) and a solution of 2M ammonia in ethanol (200 mL) were sealed in a stainless tube and stirred at 140° C. for 5 h. The reaction mixture was cooled and concentrated. The residue was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diethyl ether and the precipitated crystals were collected by filtration to give 3-aminomethyl-6-bromo-2-isobutyl-4-phenyl-1(2H)-isoquinolinone (5.6 g, 53%) as crystals.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. additionThe residue was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from diethyl ether
  9. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-0003beb3986e45b785e96ad1eaeefe3b
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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