Sodium Hydroxide → 4'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylic acid

HRID 1757274Notes

Reaction equation

HRID 1757274 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([C:29]([O:31]C)=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH3:4]>C(O)C>[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([C:29]([OH:31])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10363423Methyl 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylate

Product 1

HCID 104750474'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylic acidYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.25M sodium hydroxide solution (2.4 ml) was added to a solution of methyl 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2- carboxylate (A) (380 mg) in ethanol (5 ml). The solution was heated under reflux for 2 hours and then volatile material was removed by evaporation. The residue was dissolved in water (30 ml) and the solution acidified to pH 4 with 2M hydrochloric acid. The precipitated solid was a collected, dried under high vacuum and recrystallised from ethanol to give 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylic acid (254 mg), as white crystals, m.p. 204°-205° C.; NMR (d6 -dimethylsulphoxide (d6 -DMSO)): 1.34(t,3H), 2.9(q,2H), 5.42(s,2H), 7.1(s,1H), 7.38-7.78(complex m,10H), 7.88(d,1H), 8.15(dd,1H), 12.74(br,1H); mass spectrum (negative fast atom bombardment [-ve FAB], DMSO/glycerol (GLY): 382 (M-H)-, 172; microanalysis found: C,78.0; H,5.4; N,4.05; C25H21NO3 requires: C,78.3; H,5.5; N,3.7%.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 hours
  3. customvolatile material was removed by evaporation
  4. dissolutionThe residue was dissolved in water (30 ml)
  5. customdried under high vacuum
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-72ba136d6eec4126aa2fb5609b9a93ce
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

Loading…