Cyclopropylamine → 864866-56-8

HRID 1891250Notes

Reaction equation

HRID 1891250 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=O)=[C:4]([CH2:11]Br)[CH:3]=1.[CH:13]1([NH2:16])[CH2:15][CH2:14]1>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:9][CH:10]=1)[C:6](=[O:8])[N:16]([CH:13]1[CH2:15][CH2:14]1)[CH2:11]2

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 231581454-Bromo-2-(bromomethyl)benzoate

Product 1

HCID 23158197864866-56-8Yield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-bromo-2-(bromomethyl)benzoate (1A2) (1.62 mmol, 500 mg) and cyclopropylamine (1A3) (3.25 mmol, 185 mg) in methanol (3 ml) were heated in the microwave at 120° C. for 10 mins. The reaction mixture was concentrated and purified on silica eluting with 50-100% EtOAc/heptane to yield 5-bromo-2-cyclopropylisoindolin-1-one (1A4) 350 mg (84%); 1H NMR (400 MHz, CDCl3) δ 7.96 (d, 1H) 7.59 (d, 1H) 7.78 (s, 1H) 4.30 (s, 2H) 2.91 (m, 1H) 0.94-0.85 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified on silica eluting with 50-100% EtOAc/heptane

Sources & evidence

ORD record
ord-f84fa04b78134d7fb5053465840e2fb8
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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