Hydrochloric Acid → HCID 66745948, compound

HRID 471558Notes

Reaction equation

HRID 471558 reaction equation
[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[C:6]=1[C:7]#[N:8])([CH3:3])[CH3:2].Cl>CO.[Fe]>[NH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])[C:6]=1[C:7]#[N:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 574159382-Nitro-6-[(propan-2-yl)amino]benzonitrile

Product 1

HCID 66745948HCID 66745948, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(isopropylamino)-6-nitrobenzonitrile (Example 90c) (0.21 g, 1.02 mmol) in MeOH (9 mL) was added concentrated HCl (2 mL). Then Fe (0.17 g, 3.07 mmol) was added portionwise, and the reaction mixture was refluxed at 90° C. for 15 minutes. After cooling to room temperature, dilution with H2O (50 mL) and extraction with DCM (3×50 mL), the combined organic phases were washed with brine, dried over MgSO4 and the solvents were evaporated to give 2-amino-6-(isopropylamino)benzonitrile (0.19 g, 100%) as a brown oil which was used in the next step without any further purification. MS 176 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractiondilution with H2O (50 mL) and extraction with DCM (3×50 mL)
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvents were evaporated

Sources & evidence

ORD record
ord-a8d8d2c69a5a4d1bb50c52bd64f0a937
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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