Hydrochloric Acid → HCID 178436869, compound

HRID 893619Notes

Reaction equation

HRID 893619 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][CH3:53])[N:10]=2)[N:5]=1)[CH3:3]>CO>[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[NH:29][N:30]=[N:31][N:32]=3)=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:52][CH3:53])[N:10]=2)[N:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19890808HCID 19890808, compound

Product 1

HCID 178436869HCID 178436869, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (20 ml) was added to a hot solution of 2-ethyl-6-methoxy-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A4) (9.4 g) in methanol (30 ml). The solution was cooled and left to stand for 1 hour. The precipitated solid was collected by filtration and washed with ethyl acetate (2×100 ml) to give 2-ethyl-6-methoxy-4-[(2'-(1H-tetrazol-5-yl)-biphenyl-4-yl)methoxy]-1,5-naphthyridine hydrochloride (5.4 g), as a white solid, m.p. 181°-182° C.; NMR (d6DMSO): 1.4 (t, 3H), 3.1 (q, 2H), 4.05 (s, 3H), 5.65 (s, 2H), 7.2 (d, 2H), 7.5-7.8 (complex m, 8H), 8.55 (d, 1H); 13C NMR: (benzylic CH2) 71.8; mass spectrum (-ve FAB, DMSO/GLY): 437 (M-H)- ; microanalysis, found: C, 63.3; H, 5.0; N, 17.6; Cl, 7.3%; C25H22N6O2.HCl requires: C, 63.2; H, 4.9; N, 17.7; Cl, 7.5%.

Workup

  1. temperatureThe solution was cooled
  2. waitleft
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with ethyl acetate (2×100 ml)

Sources & evidence

ORD record
ord-1852d6e50c414b08a939af9d3f7964a8
Source dataset
uspto-grants-1992_06
Patent number
US05126344

Reaction notes

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