Benzyl Bromide → HCID 12042203, compound

HRID 1645902Notes

Reaction equation

HRID 1645902 reaction equation
Cl.[NH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][C:8]2=[O:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C1COCC1>[C:15]1([CH2:14][NH:2][C:3]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[CH2:5][CH2:6][NH:7][C:8]3=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 552533035-AMINO-3,4-DIHYDROISOQUINOLIN-1(2H)-ONE HYDROCHLORIDE

Product 1

HCID 12042203HCID 12042203, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.0 g (12.3 mmol) of 5-amino-3,4-dihydro-1(2H)-isoquinolinone, monohydrochloride in 10 ml of THF was added 2.6 g (14.76 mmol) of benzylbromide and 2 ml of triethylamine. The mixture was heated under reflux for six hours and then poured into ice water and extracted with ether. The ether extracts were washed with water, dried (MgSO4), and concentrated. The residue was chromatographed (SiO2, ether to 10:1 ether/methanol) to provide 0.6 g of the dibenzylated product and 0.95 g (31%) of the desired monobenzylated product after crystallization from ethanol; mp. 142°-144°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for six hours
  3. extractionextracted with ether
  4. washThe ether extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed (SiO2, ether to 10:1 ether/methanol)

Sources & evidence

ORD record
ord-421c297fed974e7b9f5fd89cb8ceed35
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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