Sodium Nitrite → HCID 178498465, compound

HRID 852618Notes

Reaction equation

HRID 852618 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[N:16]([O-])=O.[Na+]>CC(O)=O>[N+:13]([C:10]1[C:11]2[N:12]=[N:16][NH:1][C:2]=2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 69356421HCID 69356421, compound

Product 1

HCID 178498465HCID 178498465, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3,4-diamino-5-nitrobenzoate (D245) (2.5 g, 12 mmol, 1 equiv) in AcOH (10 ml) at room temperature was added NaNO2 (900 mg, 13 mmol, 1.1 equiv) and the resulting mixture was stirred at 60° C. for 1 h, cooled to room temperature and concentrated in vacuo. the residue was partitioned between AcOEt and a 5% aqueous citric acid solution and the layers were separated. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. Trituration of the residue in Et2O/iso-hexane gave methyl 4-nitro-1H-1,2,3-benzotriazole-6-carboxylate (D246) (2.08 g, 78%) as an orange solid which was used in the next step without further purification. [M+H]+=223.3, RT=2.31 min.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customthe residue was partitioned between AcOEt
  4. customa 5% aqueous citric acid solution and the layers were separated
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e93d9bb366784175a9f6423a07b95b34
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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