Hydrochloric Acid → HCID 86691926, compound

HRID 717769Notes

Reaction equation

HRID 717769 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)=[CH:3][CH:2]=1.Cl.[N:18]([O-])=[O:19].[Na+]>C(O)C.O>[N:18]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:8]1)=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 67378758HCID 67378758, compound

Product 1

HCID 86691926HCID 86691926, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(pyridin-4-yl)-1,2,3,4-tetrahydroquinoline (0.4 g, 0.0019 mol) in ethanol (1.7 mL) was added 1N hydrochloric acid (1.7 mL). The reaction mixture was cooled to 0° C., and a solution of sodium nitrite (0.262 g, 0.0038 mol) in water (5.5 mL) was added at 0° C. The reaction mixture was warmed to RT and stirred for 1 h. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure to obtain product as a brown colored oil (0.41 g).

Workup

  1. temperatureThe reaction mixture was warmed to RT
  2. customAfter completion of reaction (monitored by TLC), solvent
  3. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-3ebce1d84e0445418eea5e9b69935319
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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