Water → 1-(4-Aminophenyl)cyclohexanecarbonitrile

HRID 2408504Notes

Reaction equation

HRID 2408504 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.O.[NH4+].[Cl-]>CCO.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 589937681-(4-Nitro-phenyl)-cyclohexanecarbonitrile

Product 1

HCID 498745261-(4-Aminophenyl)cyclohexanecarbonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-(4-nitro-phenyl)-cyclohexanecarbonitrile (0.500 g, 2.17 mmol, as prepared in the previous step) in EtOH (6 mL) and water (6 mL) was treated with NH4Cl (1.16 g, 21.7 mmol) and Fe powder (606 mg, 10.9 mmol) and heated to 50° C. for 2 h. The cooled mixture was filtered through Celite, and the filter cake was washed with MeOH. The solvents were evaporated in vacuo. The residue was partitioned between water (50 mL) and EtOAc (75 mL), and the layers were separated. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound (488 mg, 100%) as an orange oil. The compound was used in the following step without purification. Mass spectrum (ESI, m/z): Calcd. for C13H16N2, 201.1 (M+H), found 201.3.

Workup

  1. filtrationThe cooled mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customThe solvents were evaporated in vacuo
  4. customThe residue was partitioned between water (50 mL) and EtOAc (75 mL)
  5. customthe layers were separated
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2b73bdca70d4d2c8ebd81fd86add60e
Source dataset
uspto-grants-2014_08
Patent number
US08815867B2

Reaction notes

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