Ammonia → 6-Bromo-2-naphthamide

HRID 1897571Notes

Reaction equation

HRID 1897571 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]>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

4

Reactant 2

HCID 222AmmoniaHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 574280376-Bromo-2-naphthamideYield 90.4%

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. Solvent was evaporated, and the residue was dissolved in CH2Cl2 and concentrated again. To the acid chloride intermediate was added ammonia (7N in MeOH, 13.66 ml, 96 mmol) and the mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated, diluted in ethyl acetate and filtered. The solid was rinsed with ethyl acetate and then dried. The title compound 2a (1.802 g, 90%) was isolated as beige solid. LC-MS (M+1) 251.9, t=1.34 min.

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. concentrationconcentrated again
  4. concentrationThe reaction mixture was concentrated
  5. additiondiluted in ethyl acetate
  6. filtrationfiltered
  7. washThe solid was rinsed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-a4b27b611cdc4967b3a80b3a8b702edb
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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