1,2-Dichloroethane → 3-bromo-4-hydroxy-N-methylbenzamide

HRID 63267Notes

Reaction equation

HRID 63267 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5](O)=[O:6].C(Cl)CCl.C1C=CC2N(O)N=[N:22][C:20]=2C=1.Cl.CN>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([NH:22][CH3:20])=[O:6]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 843683-Bromo-4-hydroxybenzoic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 706652403-bromo-4-hydroxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-bromo-4-hydroxybenzoic acid (Commercial eg Aldrich) (2.0 g), EDC (2.65 g), HOBT (1.41 g) and TEA (6.2 ml) in DCM (60 ml) was added methylamine hydrochloride (1.87 g). This was stirred at 25-30 C. for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate. The organics were dried (sodium sulphate) and concentrated in vacuo to yield the title compound, 0.57 g

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried (sodium sulphate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73951faffad54d90a70b4ff151fef538
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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