Hydrochloric Acid → N-(2-formyl-phenyl)-3-hydroxy-benzamide

HRID 278192Notes

Reaction equation

HRID 278192 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N-:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1.CCN(CC)CC.N1C=CC=CC=1.Cl.CS(C)=[O:34]>C(Cl)Cl>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:34])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1)=[O:1]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 8471TriethylamineHCID 86757875HCID 86757875, compound

Product 1

HCID 22627093N-(2-formyl-phenyl)-3-hydroxy-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-hydroxymethylphenyl)-3-hydroxybenzyl amide (6.5 g, 26.7 mmol) in CH2Cl2 (120 ml) at 0° C. was added NEt3 (13.0 ml, 93.4 mmol) and pyridine.SO3 complex (12.7 g, 80.1 mmol ) in DMSO, 50 mL) and the solution was stirred 4 h at 25° C. The reaction was poured into ice and 10% HCl, and the layers were partitioned. The aqueous layer was washed 2× with CH2Cl2. All CH2Cl2 layers were combined and washed with H2O, saturated NaHCO3, brine, and dried (MgSO4). The solution was filtered and concentrated in vacuo to obtain the crude product which was purified on SiO2 gel using hexane/EtOAc 7/3 to obtain the title compound.

Workup

  1. customthe layers were partitioned
  2. washThe aqueous layer was washed 2× with CH2Cl2
  3. washwashed with H2O, saturated NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto obtain the crude product which
  8. customwas purified on SiO2 gel

Sources & evidence

ORD record
ord-e8a0679d4c9b4f278f858f8edc9ba2f7
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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