Water → 2-Cyclohex-1-enyl-pyridin-3-ylamine

HRID 1711275Notes

Reaction equation

HRID 1711275 reaction equation
[C:1]1([C:7]2[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.O>CCO.CC(O)=O.CCOC(C)=O.[Fe]>[C:1]1([C:7]2[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 2

HCID 962WaterHCID 587548752-Cyclohex-1-enyl-3-nitro-pyridine

Product 1

HCID 587548302-Cyclohex-1-enyl-pyridin-3-ylamineYield 86.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 497.0 mg (2.43 mmol) of 2-cyclohex-1-enyl-3-nitro-pyridine (as prepared in the previous step) in EtOH (10 mL) and water (5 mL) was treated with AcOH (6 drops) and 679 mg (12.2 mmol) of Fe powder, and heated to 75° C. for 19 h. The mixture was diluted with EtOAc (30 mL) and washed with water (1×20 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 365 mg (86%) of the title compound as a pale yellow solid: Mass spectrum (ESI, m/z): Calcd. for C11H14N2, 175.1 (M+H), found 175.2.

Workup

  1. washwashed with water (1×20 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b97d1afc6fb744aea2cacd051b29ec47
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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