HCID 10009261, compound → HCID 178428930, compound

HRID 1757282Notes

Reaction equation

HRID 1757282 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:27]=[N:28][N:29](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:30]=3)=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.O1CCOCC1.[ClH:56]>O>[ClH:56].[CH3:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:27][N:28]=[N:29][N:30]=3)=[CH:18][CH:19]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 10009261HCID 10009261, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 178428930HCID 178428930, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline (A) (890 mg) and a 7.5M solution of hydrogen chloride dioxane (10 ml) and water (1 ml) was allowed to stand for 72 hours. Volatile material was removed by evaporation and the residue was triturated with ether (2×50 ml). The ether was decanted off and the solid residue crystallised from isopropanol to give 2-methyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline hydrochloride (370 mg), as a white solid, m.p. 188°-190° C.; NMR (d6 -DMSO): 2.92(s,3H), 5.63(s,2H), 7.21(d,2H), 7.56-7.87(m,8H), 8.07(dt,1H), 8.28(dd,1H), 8.32(dd,1H); mass spectrum [-ve FAB, DMSO/NBA]: 392 (M-H)-, 158; microanalysis found: C,66.0; H,4.6; N,15.5%; C24H19N5O.HCl.0.5H2O requires: C,65.7; H,4.8; N,16.0%.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue was triturated with ether (2×50 ml)
  3. customThe ether was decanted off
  4. customthe solid residue crystallised from isopropanol

Sources & evidence

ORD record
ord-5a5677f2991e415a8047215b40e5dc8a
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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