Lithium Hydroxide → Salicyluric Acid

HRID 1178050Notes

Reaction equation

HRID 1178050 reaction equation
[Li+].[OH-].C([O:5][C:6](=[O:18])[CH2:7][NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])C>O.C1COCC1.CO>[OH:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([NH:8][CH2:7][C:6]([OH:18])=[O:5])=[O:17]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 134599Ethyl salicylurate

Product 1

HCID 10253Salicyluric AcidYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH in water (82 mg in 2 mL of water) was added dropwise to (2-hydroxy-benzoyl amino)-acetic acid ethyl ester (110 mg, 0.49 mmol) in a mixture of THF and MeOH. The THF and MeOH were evaporated under reduced pressure and the residue was acidified using 10% citric acid solution. The product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford (2-hydroxybenzoyl amino)-acetic acid in 93% yield. 1H NMR (DMSO-D6): δ 12.8 (s, 1H), 12.2 (s, 1H), 9.2 (t, 1H), 7.9 (d, 1H), 7.5 (dt, 1H), 7.0 (d, 2H), 4.0 (d, 2H).

Workup

  1. customThe THF and MeOH were evaporated under reduced pressure
  2. extractionThe product was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfae4362460a433981e12d377123da43
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…