Potassium Cyanide → 3-Cyano-5-nitrobenzoic acid

HRID 1059734Notes

Reaction equation

HRID 1059734 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].[C-:24]#[N:25].[K+]>Cl.O>[C:24]([C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6])#[N:25]

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 2393423-Amino-5-nitrobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 219425653-Cyano-5-nitrobenzoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent4×

Procedure

3-Amino-5-nitrobenzoic acid (3.64 g, 20 mM) was dissolved in concentrated hydrochloric acid (20 ml), diluted with water (75 ml), cooled to 0°, and added over 30 minutes to a solution of NaNO2 (1.38 g, 20 mM) in water (10 ml). The pH was adjusted to 6.2 with saturated Na2CO3 solution. A mixture of CuSO4.5H2O (10 g, 42 mM) in water (40 ml) and KCN (10 g, 154 mM) in water (20 ml) was heated to 65°, the solution of diazonium salt added over 15 minutes, and the mixture refluxed for 40 minutes. After cooling, and acidifying with 2M hydrochloric acid, the organics were extracted into ethyl acetate (2×200 ml). The combined extracts were washed with aqueous NaH2PO4, water, brine, and dried over Na2SO4. Evaporation gave 3-cyano-5-nitrobenzoic acid (3.6 g, 94%).

Workup

  1. temperaturecooled to 0°
  2. temperaturewas heated to 65°
  3. temperaturethe mixture refluxed for 40 minutes
  4. temperatureAfter cooling
  5. extractionthe organics were extracted into ethyl acetate (2×200 ml)
  6. washThe combined extracts were washed with aqueous NaH2PO4, water, brine
  7. dry with materialdried over Na2SO4
  8. customEvaporation

Sources & evidence

ORD record
ord-c6171faf9b89472ebba6d58698e24417
Source dataset
uspto-grants-2003_02
Patent number
US06521612B2

Reaction notes

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