Hydrochloric Acid → HCID 178436872, compound

HRID 1587836Notes

Reaction equation

HRID 1587836 reaction equation
[ClH:1].[CH2:2]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:29]=[N:30][N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:32]=3)=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:52][CH2:53][C:54]([O:56]CC)=[O:55])[N:10]=2)[N:5]=1)[CH3:3].[OH-].[Na+]>C(O)C.O>[ClH:1].[C:54]([CH2:53][O:52][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([CH2:2][CH3:3])[CH:13]=[C:12]2[O:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[NH:32][N:31]=[N:30][N:29]=2)=[CH:20][CH:21]=1)([OH:56])=[O:55]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19756360HCID 19756360, compound

Product 1

HCID 178436872HCID 178436872, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Concentrated hydrochloric acid (2.7 ml) was added to a solution of 2-ethyl-6-(ethoxycarbonylmethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (1.0 g) in ethanol (16 ml). The solution was heated at 50° C. for 2 hours and then cooled. 4M Sodium hydroxide solution (10 ml) was added and the solution was heated at 50° C. for 30 minutes and then diluted with water (50 ml). The solution was washed with ether (25 ml) and the aqueous phase was concentrated by evaporation. Water (10 ml) was added to the residue and the suspension was stirred for 1 hour. The insoluble solid was collected by filtration and dissolved in ethanol (7 ml). Concentrated hydrochloric acid was added and the resultant precipitate was collected by filtration to give 6-(carboxymethoxy)-2-ethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine hydrochloride, m.p. 223°-225° C.; NMR (d6 -DMSO): 1.4(t, 3H), 3.1(q, 2H), 5.0(s, 2H), 5.6(s, 2H), 7.2(d, 2H), 7.4-7.8(m, 8H), 8.7(d, 1H); mass spectrum (+ve FAB, DMSO/NBA): 527 (M+H)+.

Workup

  1. temperaturecooled
  2. temperaturethe solution was heated at 50° C. for 30 minutes
  3. washThe solution was washed with ether (25 ml)
  4. concentrationthe aqueous phase was concentrated by evaporation
  5. additionWater (10 ml) was added to the residue
  6. filtrationThe insoluble solid was collected by filtration
  7. dissolutiondissolved in ethanol (7 ml)
  8. additionConcentrated hydrochloric acid was added
  9. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-5447b7a4162f4bfa9883c01f6f356475
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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