Sodium Cyanide → HCID 13509013, compound

HRID 891268Notes

Reaction equation

HRID 891268 reaction equation
N([O-])=O.[Na+].[CH3:5][C:6]1[C:12]([CH3:13])=[CH:11][C:9](N)=[C:8]([N+:14]([O-:16])=[O:15])[CH:7]=1.[Cu][C:18]#[N:19].[C-]#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.Cl.C1(C)C=CC=CC=1>[CH3:5][C:6]1[C:12]([CH3:13])=[CH:11][C:9]([C:18]#[N:19])=[C:8]([N+:14]([O-:16])=[O:15])[CH:7]=1

Participants

9

Reactant 5

HCID 8929Sodium CyanideHCID 10340Sodium CarbonateHCID 814454,5-Dimethyl-2-nitrobenzenamineHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 13509013HCID 13509013, compoundYield 42.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

0.41 g Sodium nitrite in water is added to 1 g 4,5-dimethyl-2-nitroaniline in 3 mL conc. HCl and stirred for 1 hour at +4° C. This solution is added to a mixture of 0.67 g copper (I) cyanide, 0.98 g sodium cyanide, 0.32 g sodium carbonate, 25 mL of water and 3 mL toluene. The mixture is stirred for 12 hours at room temperature and worked up to give 0.45 g 4,5-dimethyl-2-nitrobenzonitrile. 4,5-Dimethyl-2-nitrobenzonitrile is reduced with iron powder in acetic acid to yield 4,5-dimethyl-2-aminobenzonitrile. 4,5-Dimethyl-2-aminobenzonitrile is heated at reflux for 12 hours in conc. HCl to give 4,5-dimethyl-2-aminobenzoic acid. 4,5-Dimethyl-2-aminobenzoic acid is reacted with trimethylsilyl-diazomethane to yield methyl 4,5-dimethyl-2-aminobenzoate (Chem. Pharm. Bull. Vol. 29, 1475 (1981)).

Workup

  1. stirringThe mixture is stirred for 12 hours at room temperature

Sources & evidence

ORD record
ord-4737f5530bd34c3bb1fbe94e8b045c05
Source dataset
uspto-grants-2006_02
Patent number
US07002022B2

Reaction notes

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