Bromine → HCID 68865987, compound

HRID 1725988Notes

Reaction equation

HRID 1725988 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[Br:16]Br>C(Cl)(Cl)Cl.CN(C=O)C>[NH2:1][C:2]1[C:11]([Br:16])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 24408BromineHCID 68862599HCID 68862599, compound

Product 1

HCID 68865987HCID 68865987, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 2-amino-1-naphthoate (0.5 g, 2.4 mmol) in chloroform (5 mL) and DMF (1 mL) was treated with bromine (0.125 mL, 2.4 mmol) for 30 minutes, concentrated, and dissolved in ethyl acetate. The organic layer was washed with NaHCO3 (3×), brine (3×) and water (3×), dried (Na2SO4), filtered, and concentrated to provide the desired product (0.69 g). MS (DCI) m/e 284, 286 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in ethyl acetate
  3. washThe organic layer was washed with NaHCO3 (3×), brine (3×) and water (3×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9e118611fa6d40beb694c39bc8d0b009
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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