Sodium Hydroxide → HCID 20094243, compound

HRID 273740Notes

Reaction equation

HRID 273740 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]3[O:24][C:23]([C:25]4[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=4[C:27]([O:29]C)=[O:28])=[N:22][C:21]=3[CH:35]=2)[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1)[CH3:4]>CO>[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]3[O:24][C:23]([C:25]4[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=4[C:27]([OH:29])=[O:28])=[N:22][C:21]=3[CH:35]=2)[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1)[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20094248HCID 20094248, compound

Product 1

HCID 20094243HCID 20094243, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1M Sodium hydroxide solution (5.0 ml) was added to a solution of methyl 2-[5-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy)methyl)benzoxazol-2-yl]benzoate (A) (443 mg) in methanol (20 ml) and the solution was left to stand for 72 hours. Volatile material was removed by evaporation and the residue was dissolved in methanol (10 ml). Water (40 ml) was added and the solution was neutralised with 1M acetic acid (5 ml). The precipitated solid was collected by filtration, dried by azeotroping with ethanol and triturated with ether to give 2-[5-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy)methyl)benzoxazol-2-yl]benzoic acid (152 mg), as a white powder, m.p. 229°-231° C; NMR (d6 -DMSO): 1.2(t, 3H), 1.7-1.85(m, 4H), 2.55-2.8(m, 6H), 5.3(s, 2H), 6.8(s, 1H), 7.55(dd, 1H), 7.65-7.9(m, 6H); mass spectrum (+ve FAB, DMSO/methanol/m-nitrobenzyl alcohol (NBA)): 429 (M+H)+ ; microanalysis, found: C, 70.7; H, 5.6; N, 6.1%; C26H24N2O4.0.5H2O requires: C, 71.2; H, 5.7; N, 6.4%.

Workup

  1. waitthe solution was left
  2. customVolatile material was removed by evaporation
  3. dissolutionthe residue was dissolved in methanol (10 ml)
  4. additionWater (40 ml) was added
  5. filtrationThe precipitated solid was collected by filtration
  6. customdried
  7. customby azeotroping with ethanol
  8. customtriturated with ether

Sources & evidence

ORD record
ord-1a968c10b2e24f008a2ab04c6c2416a9
Source dataset
uspto-grants-1995_02
Patent number
US05387592

Reaction notes

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