Hydrochloric Acid → HCID 86691934, compound

HRID 717791Notes

Reaction equation

HRID 717791 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[N:19]([O-])=[O:20].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([N:19]=[O:20])[CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 24267036HCID 24267036, compound

Product 1

HCID 86691934HCID 86691934, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-fluorophenyl)-1,2,3,4-tetrahydroquinoline (0.25 g, 0.0011 mol) in ethanol (1.2 mL) was added 1N hydrochloric acid (1.2 mL). The reaction mixture was cooled to 0° C., and to this a cold solution of sodium nitrite (0.151 g, 0.0022 mol) in water (3.0 mL) was added at the same temperature. 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 (0.27 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-c036d2f614fd4b8284e27d6f01a7c5b6
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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