1,2-Dichloroethane → 6-bromo-N-methoxy-N-methyl-2-Naphthalenecarboxamide

HRID 2115770Notes

Reaction equation

HRID 2115770 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.[CH3:15][O:16][NH:17][CH3:18].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:15][O:16][N:17]([CH3:18])[C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[CH:8]=1)=[O:14]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14232N,O-DimethylhydroxylamineHCID 757711-HydroxybenzotriazoleHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 598132256-bromo-N-methoxy-N-methyl-2-Naphthalenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-bromo-naphthalene-2-carboxylic acid (0.6 g, 2.4 mmol) and O,N-dimethyl-hydroxylamine (0.28 g, 2.87 mmol) in CH2Cl2 (20 mL), was added EDC (0.55 g, 2.87 mmol), HOBt (0.39 g, 2.87 mmol) and TEA (0.66 mL, 4.8 mmol). The reaction was stirred at RT overnight. The solvent was removed in vacuo and the crude material was purified by silica gel column chromatography with (20-40% EtOAc/hexane) to give the titled compound as a white solid. MS (ESI, pos. ion) m/z: 294.0 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude material was purified by silica gel column chromatography with (20-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-8de5ef690591435d8a297a5550e992e7
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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