Methyl 6-Amino-2-naphthoate → Methyl 6-amino-5-bromo-2-naphthoate

HRID 1920514Notes

Reaction equation

HRID 1920514 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.[Br-:16].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C1COCC1>[NH2:1][C:2]1[C:3]([Br:16])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 11995029Methyl 6-Amino-2-naphthoateHCID 21124087Pyridiniumtribromide

Product 1

HCID 59157959Methyl 6-amino-5-bromo-2-naphthoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 6-amino-2-naphthoate (0.5 g) in THF (10 ml) was added pyridinium tribromide (0.87 g). The reaction mixture was stirred at 0° C. for 1 h after which it was then filtered through a pad of SiO2 and washed with hexane. The organic washings were evaporated to dryness and the residue was purified by flash chromatography eluting with hexane to afford the titled compound.

Workup

  1. filtrationwas then filtered through a pad of SiO2
  2. washwashed with hexane
  3. customThe organic washings were evaporated to dryness
  4. customthe residue was purified by flash chromatography
  5. washeluting with hexane

Sources & evidence

ORD record
ord-1f1da8a87d524cfbb102f4a7f7fd7e67
Source dataset
uspto-grants-2012_05
Patent number
US08168815B2

Reaction notes

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