Carbon Dioxide → 6-bromo-N-methoxy-N-methyl-2-Naphthalenecarboxamide

HRID 55753Notes

Reaction equation

HRID 55753 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].C(=O)=O.[Br:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([C:26](Cl)=[O:27])[CH:20]=[CH:19]2>O.ClCCl>[Br:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([C:26]([N:3]([O:4][CH3:5])[CH3:2])=[O:27])[CH:20]=[CH:19]2

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 218796066-Bromo-2-naphthoyl chloride

Product 1

HCID 598132256-bromo-N-methoxy-N-methyl-2-NaphthalenecarboxamideYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

N,O-Dimethylhydroxylamine Hydrochloride (41.3 g, 423 mmol, 1.5 equiv.) was dissolved in distilled water (200 mL) and potassium carbonate (117 g, 3.0 equiv.) was added portion wise (CO2 evolution). Water (300 mL) and dichloromethane (200 mL) was added and a solution of 6-bromo-2-naphthoyl chloride (76.1 g, 282 mmol, 1.00-equiv.) in dichloromethane (300 mL) was added portion wise to this mixture while stirring. The reaction mixture was stirred 1 hour. The organic layer was separated, dried over sodium sulphate, filtrated, concentrated and dried in vacuum overnight, yielding 6-bromo-N-methoxy-N-methyl-2-naphthamide (82.9 g, 100%) as a brown solid.

Workup

  1. stirringThe reaction mixture was stirred 1 hour
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. customdried in vacuum overnight

Sources & evidence

ORD record
ord-4ea65913dc65452e991163fb0e0918b6
Source dataset
uspto-grants-2016_09
Patent number
US09433609B2

Reaction notes

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