Hydrochloric Acid → 1,5-Naphthyridine--hydrogen chloride (1/1)

HRID 1587828Notes

Reaction equation

HRID 1587828 reaction equation
[ClH:1].C([C:4]1[CH:13]=[C:12](OCC2C=CC(C3C=CC=CC=3C3N=NN(C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)N=3)=CC=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OCC(OCC)=O)[N:10]=2)[N:5]=1)C>C(O)C>[ClH:1].[N:5]1[C:6]2[C:11](=[N:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19756360HCID 19756360, compound

Product 1

HCID 162174631,5-Naphthyridine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Concentrated hydrochloric acid (1.6 ml) was added to a suspension of 2-ethyl-6-(ethoxycarbonylmethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (0.61 g) in ethanol (9.7 ml) and the resulting solution was stirred for three hours. The precipitated solid was collected by filtration and recrystallised from methanol to give 2-ethyl-6-(ethoxycarbonylmethoxy)-4-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine hydrochloride (0.139 g), as a white powder, m.p. 191°-193° C.; NMR (d6 -DMSO): 1.0(t,3H), 1.4(t,3H), 3.1(q,2H), 4.0(q,2H), 5.0(s,2H), 5.6(s,2H), 7.2(d,2,H), 7.6(m,8H), 8.7(d,1H); mass spectrum (+ve FAB, DMSO/NBA): 511 (M+H)+.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customrecrystallised from methanol

Sources & evidence

ORD record
ord-947596dcf2934aadada73a9bdd931624
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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