Hydrochloric Acid → HCID 178418662, compound

HRID 5682

Reaction equation

HRID 5682 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 (1.43 g) in water (10 ml) 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; NMR similar to the product obtained from Example 10.

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-832ff61cff804954b0b824263d4250bb
Source dataset
uspto-grants-1993_09
Patent number
US05245035

Linked notes

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