Sodium Hydroxide → 4-[2-(3,6-dihydro-2H-pyridin-1-yl)-ethyl]-aniline

HRID 24923Notes

Reaction equation

HRID 24923 reaction equation
O.O.[Sn](Cl)Cl.[N:6]1([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:11][CH:10]=[CH:9][CH2:8][CH2:7]1.[OH-].[Na+]>C(O)(=O)C.Cl.O>[N:6]1([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:7][CH:8]=[CH:9][CH2:10][CH2:11]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrate2×HCID 225697854-[2-(3,6-Dihydro-2h-pyridin-1-yl)-ethyl]-nitrobenzene

Product 1

HCID 219185824-[2-(3,6-dihydro-2H-pyridin-1-yl)-ethyl]-aniline

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

2.5 g (11.1 mmol) of tin dichloride dihydrate are added at ambient temperature to a solution of 1.5 g (6.46 mmol) of 4-[2-(3,6-dihydro-2H-pyridin-1-yl)-ethyl]-nitrobenzene, prepared analogously to Example 254, in 7 ml of glacial acetic acid and 2.5 ml of concentrated hydrochloric acid. The mixture is heated for 4 hours to 100° C., then another 2.5 g (11.1 mmol) of tin dichloride dihydrate are added and the mixture is heated for 12 hours to 100° C. After cooling the solvent is eliminated in vacuo and the residue taken up in water. The mixture is made alkaline with 4N sodium hydroxide solution and extracted with dichloromethane. After removal of the solvent in vacuo the product is obtained as an oil.

Workup

  1. temperatureThe mixture is heated for 4 hours to 100° C.
  2. temperaturethe mixture is heated for 12 hours to 100° C
  3. temperatureAfter cooling the solvent
  4. extractionextracted with dichloromethane
  5. customAfter removal of the solvent in vacuo the product
  6. customis obtained as an oil

Sources & evidence

ORD record
ord-c1a31f4425c94b6abe748584a3ac8945
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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