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Hydrochloric Acid → 3-(4-Fluorophenyl)-6-methyl-1-nitroso-1,2,3,4-tetrahydroquinoline

HRID 717760
Notes
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Reaction equation

HRID 717760 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]=[C:14]([CH3:18])[CH:15]=3)[NH:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[N:20]([O-])=[O:21].[Na+]>C(O)C.O>[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]=[C:14]([CH3:18])[CH:15]=3)[N:10]([N:20]=[O:21])[CH2:9]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 242670393-(4-Fluorophenyl)-6-methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 866919223-(4-Fluorophenyl)-6-methyl-1-nitroso-1,2,3,4-tetrahydroquinolineYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962
Water
Solvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-(4-fluorophenyl)-6-methyl-1,2,3,4-tetrahydroquinoline (0.28 g, 0.00166 mol) in ethanol (1 mL) was added 1N hydrochloric acid (1 mL), and the reaction mixture was cooled to 0° C. Sodium nitrite (0.160 g, 0.00232 mol) in water (3 mL) was added at 0° C., and the mixture stirred for 1 h at RT. The reaction was monitored by TLC. After completion, solvent was removed under reduced pressure to obtain product as a brown colored oil (0.28 g, 89% yield).

Workup

  1. customAfter completion, solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e594863405cf4486ae0156d9af114ea3
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193728B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes