Lithium Hydroxide → 4-Fluoro-3-(morpholine-4-sulfonyl)benzoic acid

HRID 277571Notes

Reaction equation

HRID 277571 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][C:5]=1[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:15]>O.CO>[F:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:15])=[O:16]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 700043Methyl 4-fluoro-3-(morpholin-4-ylsulfonyl)benzoate

Product 1

HCID 6927164-Fluoro-3-(morpholine-4-sulfonyl)benzoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of lithium hydroxide (1.56 g, 37.3 mmol) in water (5 mL) was added to a stirred solution of 4-fluoro-3-(morpholine-4-sulfonyl)-benzoic acid, methyl ester (Example 5, 2.26 g, 7.45 mmol) in methanol (50 mL) / water (10 mL) at 0° C. After 4 hours, the clear solution was quenched with aqueous hydrochloric acid (2M, 10 mL). Concentration in vacuo to remove the methanol afforded a white precipitate. Filtration and drying afforded the title compound as a white powder (1.89 g, 88% yield): 1HNMR (CDCl3) δ3.21 (td, J=7, 1.5 Hz, 4H), 3.75 (td, , J=7, 1.5 Hz , 4H), 3.98 (s, 3H), 7.28 (dd, J=18, 15 Hz, 1H), 8.28 (ddd, J=7, 5, 2 Hz, 1H), 8.51 (dd, J=7, 2 Hz, 1H): MS (ESI) [M−H]− at m/z 303.

Workup

  1. customthe clear solution was quenched with aqueous hydrochloric acid (2M, 10 mL)
  2. concentrationConcentration in vacuo
  3. customto remove the methanol
  4. customafforded a white precipitate
  5. filtrationFiltration
  6. customdrying

Sources & evidence

ORD record
ord-636a9c1dd665456c8919d9a5847b34b5
Source dataset
uspto-grants-2002_03
Patent number
US06355633B1

Reaction notes

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