Hydrochloric Acid → HCID 178418662, compound

HRID 1757287Notes

Reaction equation

HRID 1757287 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:28]=[N:29][N:30]([Sn](CCCC)(CCCC)CCCC)[N:31]=3)=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].C(C1C=C(OCC2C=CC(C3C(C#N)=CC=CC=3)=CC=2)C2C(=CC=CC=2)N=1)C.C([Sn](N=[N+]=[N-])(CCCC)CCCC)CCC.C([Sn]([Cl:102])(CCCC)CCCC)CCC.[N-]=[N+]=[N-].[Na+].N([O-])=O.[Na+].Cl.S(=O)(=O)(O)N>C1(C)C=CC=CC=1.O>[ClH:102].[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Participants

11

Reactant 8

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 4984872Tributyltin azideHCID 150208494'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrileHCID 193899352-ethyl-4-[(2'-(2-tributylstannyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinolineHCID 23668193Sodium Nitrite

Product 1

HCID 178418662HCID 178418662, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1140TolueneSolvent2×

Procedure

A solution of 2-ethyl-4-[(2'-(2-tributylstannyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline in toluene (15 ml), prepared in situ by refluxing for 90 hours a mixture of 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile (0.9 g) and a solution of tributyltin azide in toluene (15 ml) [the latter prepared by reaction of tributyltin chloride (3.3 g) and sodium azide (1.13 g) in water (22.5 ml) at ambient temperature for 4 hours, followed by extraction with toluene and azeotropic removal of water from the extract to leave a volume of 15 ml], was added slowly over 1 hour to a solution of sodium nitrite (2.5 g) in water (10 ml) containing 12% w/v hydrochloric acid (10 ml), maintaining the temperature of the mixture below 5° C. A solution of sulphamic acid (1.43g) in water (10ml) was then added, maintaining the temperature below 5° C., and the mixture stirred for 1 hour. The resultant suspended semi-solid was collected by filtration and washed with water (3×10 ml), followed by toluene (10 ml). The semi-solid was then added to tetrahydrofuran (THF) (40 ml), which caused the product to dissolve and then crystallise as a white solid. After cooling for one hour the solid was collected by filtration, washed with THF (5 ml) and dried to give 2-ethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline hydrochloride; m.p. 179°-180° C. (dec.); NMR (d6 -DMSO): 1.46(t, 3H), 3.18(q,2H), 5.68(s,2H), 7.22(d,2H), 7.5-7.8(m,7H), 7.83(t,1H), 8.08(t,1H), 8.18(d,1H), 8.32(d,1H).

Workup

  1. temperatureby refluxing for 90 hours
  2. extractionfollowed by extraction with toluene and azeotropic removal of water from the
  3. extractionextract
  4. customto leave a volume of 15 ml],
  5. additioncontaining 12%
  6. temperaturemaintaining the temperature of the mixture below 5° C
  7. temperaturemaintaining the temperature below 5° C.
  8. filtrationwas collected by filtration
  9. washwashed with water (3×10 ml)
  10. additionThe semi-solid was then added to tetrahydrofuran (THF) (40 ml), which
  11. dissolutionto dissolve
  12. customcrystallise as a white solid
  13. temperatureAfter cooling for one hour the solid
  14. filtrationwas collected by filtration
  15. washwashed with THF (5 ml)
  16. customdried

Sources & evidence

ORD record
ord-b14a4772f92a4e12856bf4c6a52d3039
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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