Water → 2,6-dihydroxy-N,N-dimethylbenzamide

HRID 660610Notes

Reaction equation

HRID 660610 reaction equation
C[O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[C:4]=1[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:4]=1[C:5]([N:7]([CH3:9])[CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 32670112,6-dimethoxy-N,N-dimethylbenzamide

Product 1

HCID 222719252,6-dihydroxy-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dimethoxy-N,N-dimethylbenzamide (100 mg, 0.48 mmol) in methylene chloride (2.5 mL) is added BBr3 (1.0M in methylene chloride, 1.4 mL) dropwise and the mixture is stirred at RT for 18 h. Water is added and the suspension is extracted with EtOAc. The organic layer is washed with water and brine, and dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound: 1H NMR (DMSO-d6) δ 9.35 (s, 2H), 6.93-6.89 (t, J=8.34 Hz, 1H), 6.29-6.27 (d, J=8.09 Hz, 2H), 2.89 (s, 3H), 2.86 (s, 3H).

Workup

  1. extractionthe suspension is extracted with EtOAc
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-34a06a4db46a4fe4a0989796ef369007
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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