Hydrochloric Acid → HCID 22136223, compound

HRID 471580Notes

Reaction equation

HRID 471580 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]=1[C:6]#[N:7])([O-])=O.Cl>CO.[Fe]>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67397106HCID 67397106, compound

Product 1

HCID 22136223HCID 22136223, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-6-(phenoxy)benzonitrile (Example 113c) (1.94 g, 8.08 mmol) in MeOH (164 mL) was slowly added concentrated HCl (7.23 mL) followed by iron powder (1.58 g, 28.3 mmol). The reaction was refluxed for 30 min and concentrated in vacuo. The residue was dissolved in EtOAc and washed with 1N NaOH, water and brine. The organic layer was dried over MgSO4, filtered, concentrated and purified by flash chromatography 1:1 Hexane:EtOAc to yield 2-amino-6-phenoxybenzonitrile (384 mg, 22.6%). 1H NMR (400 MHz, MeOD) δ 5.97 (d, J=8.3 Hz, 1H), 6.50 (d, J=8.6 Hz, 1H), 7.06 (m, 2H), 7.18 (m, 2H), 7.40 (m, 2H). MS 210 (MH+).

Workup

  1. temperatureThe reaction was refluxed for 30 min
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 1N NaOH, water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography 1:1 Hexane

Sources & evidence

ORD record
ord-d37fc6873b884ae0ac5adf38164e2449
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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