Sodium Hydroxide → HCID 178428933, compound

HRID 2254698Notes

Reaction equation

HRID 2254698 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=2)=[C:6]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=2)[CH:5]=[C:4]([CH3:38])[N:3]=1.[OH-].[Na+]>C(O)C>[C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:7]2[C:2]([CH3:1])=[N:3][C:4]([CH3:38])=[CH:5][C:6]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=2)=[CH:13][CH:12]=1)([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 178468749HCID 178468749, compound

Product 1

HCID 178428933HCID 178428933, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Dimethyl-3-(4-ethoxycarbonylphenyl)-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (50 mg) was added to a mixture of 1M sodium hydroxide solution (0.2 ml) and ethanol (2 ml), and the mixture was heated at reflux for 1 hour. Additional 1M sodium hydroxide solution (0.1 ml) was added and the mixture was heated at reflux for a further 30 minutes. Volatile material was removed by evaporation. The residue was dissolved in water (10 ml) and the mixture was extracted with dichloromethane. The aqueous phase was separated and adjusted to pH 5 with 1M citric acid solution. The resultant precipitate was collected by filtration to give 3-(4-carboxyphenyl)-2,6-dimethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine as a solid, m.p. 207°-210° C. (decomposition); NMR (d6 -DMSO): 2.1(s, 3H), 2.44(s, 3H), 5.13(s, 2H), 6.94(s, 1H), 7.03(d, 2H), 7.15(d, 2H), 7.38(d, 2H), 7.55(m, 4H), 9.8(d, 2H); mass spectrum (+ve FAB, methanol/nitrobenzyl alcohol): 478(M+H)+ ; microanalysis, found: C, 66.6, H, 5.0; N, 13.9%; C28H23N5O3.1.5H2O requires: C, 66.7; H, 5.1; N, 13.9%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe mixture was heated
  4. temperatureat reflux for a further 30 minutes
  5. customVolatile material was removed by evaporation
  6. dissolutionThe residue was dissolved in water (10 ml)
  7. extractionthe mixture was extracted with dichloromethane
  8. customThe aqueous phase was separated
  9. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-ac94ceb8e1eb4428b0aa24e576a539eb
Source dataset
uspto-grants-1993_08
Patent number
US05236936

Reaction notes

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