Ammonia → HCID 59459870, compound

HRID 587780Notes

Reaction equation

HRID 587780 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[Cl:12])[C:5](OC)=[O:6].C(ON=O)(C)(C)C.NC1C(Br)=CC(C(OC)=O)=CC=1Br.N>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[Cl:12])[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 10906Tert-Butyl nitriteHCID 11001350Methyl 4-amino-3,5-dibromobenzoateHCID 86722585HCID 86722585, compound

Product 1

HCID 59459870HCID 59459870, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Methyl 3,5-dibromo-4-chlorobenzoate: CuCl2 (2.82 g, 21.0 mmol) in MeCN (30 mL) was stirred at 80° C. for 30 min. To this mixture tert-butylnitrite (2.7 mL, 23 mmol) was then added dropwise at same temperature and the mixture was stirred for another 10 min. Methyl 4-amino-3,5-dibromobenzoate (5.0 g, 16 mmol) in MeCN (30 mL) was added dropwise to the reaction mixture and then stirred at 80° C. for 30 min. The reaction mixture was brought to ambient temperature and an aqueous ammonia solution (20 mL) was added to the reaction mixture and extracted with petroleum ether. The organic layer was washed with brine followed by water, dried (Na2SO4), filtered and concentrated to afford the title compound as an off white solid (4.5 g, 84%). 1H NMR (300 MHz, DMSO-d6) δ 8.21 (s, 2H), 3.94 (s, 3H); ESIMS m/z 326 ([M]+); IR (thin film) 1732, 746 cm−1.

Workup

  1. stirringstirred at 80° C. for 30 min
  2. customwas brought to ambient temperature
  3. extractionextracted with petroleum ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-85df5f22fb8740e2a276f988e4f9537a
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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