Ammonia → 6-Bromo-2-naphthamide

HRID 1897818Notes

Reaction equation

HRID 1897818 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.[NH3:15].CO>S(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH2:15])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 574280376-Bromo-2-naphthamideYield 90%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

6-bromo-2-naphthoic acid (2 g, 7.97 mmol) was stirred in thionyl chloride (13.28 ml) at 70° C. for 16 h. After concentration in vacuo, the residue was rediluted in CH2Cl2 and concentrated again. To the acid chloride intermediate was added ammonia in MeOH (7 M, 13.66 ml, 96 mmol) and the mixture was stirred at room temperature for 3 h. The mixture was then concentrated. The residue was taken up in AcOEt, filtered, rinsed with AcOEt and then dried over MgSO4, filtered and concentrated in vacuo. The title compound (1.802 g, 90%) was isolated as a beige solid. LC-MS (M+1) 251.9, t=1.34 min.

Workup

  1. concentrationAfter concentration in vacuo
  2. additionthe residue was rediluted in CH2Cl2
  3. concentrationconcentrated again
  4. concentrationThe mixture was then concentrated
  5. filtrationfiltered
  6. washrinsed with AcOEt
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10031a30fea942cc985e5c374d59f97a
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

Loading…