Lithium iodide → 3-({[3-Methyl-4-(propan-2-yl)phenoxy]acetyl}amino)benzoic acid

HRID 2358281Notes

Reaction equation

HRID 2358281 reaction equation
[CH:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18]C)=[O:17])=[O:11])=[CH:6][C:5]=1[CH3:25])([CH3:3])[CH3:2].[I-].[Li+]>N1C=CC=CC=1>[CH:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([OH:18])=[O:17])=[O:11])=[CH:6][C:5]=1[CH3:25])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 730025Methyl 3-{[(4-isopropyl-3-methylphenoxy)acetyl]amino}benzoate

Product 1

HCID 97974423-({[3-Methyl-4-(propan-2-yl)phenoxy]acetyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 3-[2-(4-isopropyl-3-methyl-phenoxy)acetylamino]benzoate (948 mg, 2.78 mmol) and lithium iodide (3.72 g, 27.8 mmol) in anhydrous pyridine (15 mL) was heated to reflux for 20 h, then cooled and evaporated. The residue was taken up in water, and extracted twice with ethyl acetate. The extracts were washed with 1 N hydrochloric acid and brine, combined, dried over magnesium sulfate, filtered and evaporated to afford a semisolid mixture. The mixture was fractionally crystallized using ether-hexane to afford the title product as a solid, collected by filtration and dried under vacuum, m.p. 188-189° C. (772 mg, 2.36 mmol, 85%). 1H NMR (300 MHz, CDCl3): δ 8.44 (1H, br s), 8.03-7.96 (2H, m), 7.79 (1H, dt, J=7.7, 1.3 Hz), 7.39 (1H, t, J=7.9 Hz), 7.14 (1H, d, J=8.8 Hz), 6.79-6.73 (2H, m), 4.54 (2H, s), 3.03 (1H, heptet, J=7.0 Hz), 2.28 (3H, s), 1.14 (6H, d, J=7.0 Hz). MS (ESI): m/e 330 (3), 329 (21), 328 (100). Elemental analysis: calc. for C19H21NO4.0.1H2O C 69.33, H 6.49, N 4.25; observed C 69.22, H 6.53, N 4.17.

Workup

  1. temperatureto reflux for 20 h
  2. temperaturecooled
  3. customevaporated
  4. extractionextracted twice with ethyl acetate
  5. washThe extracts were washed with 1 N hydrochloric acid and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto afford a semisolid mixture
  10. customThe mixture was fractionally crystallized

Sources & evidence

ORD record
ord-6d0de0834f274ca1a3b2460343802d3a
Source dataset
uspto-grants-2010_07
Patent number
US07763656B2

Reaction notes

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