Sodium Hydroxide → 5-Amino-2-chlorobenzonitrile

HRID 1181946Notes

Reaction equation

HRID 1181946 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5].[OH-].[Na+]>C(O)C>[C:4]([C:3]1[CH:6]=[C:7]([CH:8]=[CH:9][C:2]=1[Cl:1])[NH2:10])#[N:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 109972345-Amino-2-chlorobenzonitrileYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloro-5-nitrobenzonitrile (25 g, 137 mmol) was dissolved in ethanol (275 mL). Stannous chloride dihydrate (154.5 g, 0.685 M) was added and the mixture stirred at 70° C. for 30 min. The mixture was then cooled to room temperature and poured into crushed ice. The mixture was made basic with solid sodium hydroxide. This mixture was extracted with ethyl acetate (3×100 mL). The extracts were combined, washed with brine, dried (MgSO4), concentrated and the residue dried under vacuum and recrystallized from ethanol to yield light brown needles (10.6 g, 51%).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. additionpoured
  3. custominto crushed ice
  4. extractionThis mixture was extracted with ethyl acetate (3×100 mL)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customthe residue dried under vacuum
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dcaadd7b16d44cd0b1d06764a30065ee
Source dataset
uspto-grants-2007_10
Patent number
US07285662B2

Reaction notes

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