Allyl bromide → HCID 86719546, compound

HRID 2208759Notes

Reaction equation

HRID 2208759 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C=O)C>[CH2:23]([N:13]([CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:4]1[C:5]([CH3:12])=[C:6]([CH:11]=[C:2]([Cl:1])[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8])[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 70873719HCID 70873719, compound

Product 1

HCID 86719546HCID 86719546, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 5-chloro-3-(cyclopentylamino)-2-methylbenzoate (1.2 g, 4.46 mmol) was dissolved in DMF (12 mL) and cooled to 0° C. NaH (0.21 g, 8.92 mmol) was added after 10 minutes and allyl bromide (1.07 g, 8.9 mmol) was added. The reaction mixture was stirred at room temperature for 4 h and then heated at 80 0° C. for 18 h. The reaction was quenched with ice water and extracted with ethyl acetate. Combined organic layers were dried, concentrated giving crude methyl 3-(allyl(cyclopentyl)amino)-5-chloro-2-methylbenzoate (0.4 g, 29.4%).

Workup

  1. temperatureheated at 80 0° C. for 18 h
  2. customThe reaction was quenched with ice water
  3. extractionextracted with ethyl acetate
  4. customCombined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f12829de176c4fb0818212140342c2df
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…