p-Xylyl bromide → HCID 16657461, compound

HRID 1866865Notes

Reaction equation

HRID 1866865 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:16][C:17]2[CH:24]=[CH:23][C:20]([CH3:21])=[CH:19][CH:18]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 16657461HCID 16657461, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Benzyloxy-2(1H)-pyridone (3.0 g, 0.015 mol), 4-methylbenzyl bromide (3.15 g, 0.17 mol), and potassium carbonate (3.0 g, 0.022 mol) were heated at 80° C. for 2 hours. Contents were allowed to cool, diluted with water and a solid (5.52 g) was filtered. FABHRMS m/z 306.1494 (M+H, C20H20NO2 requires 306.1494). 1H NMR (CDCl3/300 MHz): 7.50-7.40 (m, 5H); 7.20-7.05 (m, 5H); 6.07-6.00 (m, 1H); 5.95-5.90 (m, 1H); 5.05 (s, 2H); 5.00 (s, 2H); 2.32 (s, 3H).

Workup

  1. temperatureto cool
  2. filtrationa solid (5.52 g) was filtered

Sources & evidence

ORD record
ord-ad647075cab64917b5d65d73b87ce39e
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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