Water → 2-(4,4-Dimethyl-cyclohex-1-enyl)-pyridin-3-ylamine

HRID 1711271Notes

Reaction equation

HRID 1711271 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH2:3]1.O>CCO.CC(O)=O.[Fe]>[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH2:3]1

Participants

6

Reactant 2

HCID 962WaterHCID 685051192-(4,4-Dimethyl-cyclohex-1-enyl)-3-nitro-pyridine

Product 1

HCID 587548632-(4,4-Dimethyl-cyclohex-1-enyl)-pyridin-3-ylamineYield 102.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 90.0 mg (0.387 mmol) of 2-(4,4-dimethyl-cyclohex-1-enyl)-3-nitro-pyridine (as prepared in the previous step) in EtOH (10 mL) and water (5 mL) was treated with AcOH (3 drops) and 121 mg (2.17 mmol) of Fe powder then heated to 70° C. for 1.5 h. The mixture was quenched with saturated aqueous NaHCO3 (20 mL) and extracted with CH2Cl2 (3×40 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to afford 80.0 mg (100%) of the title product as a tan glass: Mass spectrum (ESI, m/z): Calcd. for C13H18N2, 203.2 (M+H), found 203.2.

Workup

  1. customThe mixture was quenched with saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with CH2Cl2 (3×40 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-619477557b6a4ede99a05b328df89f13
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

Loading…