Sodium Hydroxide → 2-Amino-5-methylbenzonitrile

HRID 2076964Notes

Reaction equation

HRID 2076964 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[C:7]#[N:8].Cl[Sn]Cl.[OH-].[Na+]>Cl.CCO>[NH2:10][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 5607435-Methyl-2-nitrobenzonitrile

Product 1

HCID 2427782-Amino-5-methylbenzonitrileYield 99.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in portions to a stirred solution of SnCl2 (11.22 g, 59.2 mmol) in conc. HCl (12 mL) and EtOH (12 mL). The reaction temperature was maintained at 20-30° C. using an ice bath. The reaction mixture was then stirred at room temperature for 1 h and poured into an ice cold aqueous solution of NaOH (6N, app. 30 mL) to neutralize to pH7. The product was extracted into EtOAc, washed with brine, dried over MgSO4 and concentrated to provide the title product (1.56 g, 99%) as a yellow-brown solid. 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 3H), 5.79 (bs, 2H), 6.68-6.71 (d, 1H), 7.10-7.13 (dd, 1H), 7.15 (s, 1H). 13C NMR (DMSO-d6) δ 20.13, 93.99, 116.12, 118.94, 125.38, 132.32, 135.76, 150.21. MS 133 (MH+).

Workup

  1. extractionThe product was extracted into EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8f05fcea28f48109704229eab3430f4
Source dataset
uspto-grants-2011_04
Patent number
US07928111B2

Reaction notes

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