Benzyl Bromide → HCID 54357009, compound

HRID 583376Notes

Reaction equation

HRID 583376 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-]>CC(C)=O>[CH2:13]([O:5][C:4](=[O:6])[C:3]1[C:7]([CH3:12])=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[NH2:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 2757742-amino-3,6-dimethylbenzoic acid

Product 1

HCID 54357009HCID 54357009, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 940 mg (5.73 mmol) of 2-amino-3,6-dimethylbenzoic acid, 0.750 ml (6.3 mmol) of benzyl bromide, 1.04 g (7.5mmole) of potassium carbonate and 40 mg (0.27mmole) of soium iodide in 20 ml of acetone was heated to reflux for 20 hr. The resulting mixture was then concentrated in vacuo and the residue was chronatoghed with EtOAc/Hexane (1:50) as eluant to provide 697 mg (48%) of the desired product as a yellow oil. Electrospray Mass Spec 256 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hr
  3. concentrationThe resulting mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-1008da67a5e54197b2b7481a8f9f2134
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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