Nitric Acid → HCID 14916653, compound

HRID 2401484Notes

Reaction equation

HRID 2401484 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][CH3:16].[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:10][C:6]=2[CH:5]=[C:4]([N+:17]([O-:19])=[O:18])[C:3]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14916652HCID 14916652, compound

Product 1

HCID 14916653HCID 14916653, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Methyl 4-chloro-5-methoxybenzofuran-2-carboxylate was dissolved in conc. sulphuric acid (58 mL) with stirring in an ice bath then conc. nitric acid was added dropwise, maintaining the temperature below 5° C. The reaction was then stirred at room temperature for 2.5 h. The reaction was added to ice water (500 mL) over 2 h. The resulting solid was filtered and washed with water until neutral. The solid was dried to afford methyl 4-chloro-5-methoxy-6-nitrobenzofuran-2-carboxylate (6.3 g, 91%), which was taken through to the next step with no further purification.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. stirringThe reaction was then stirred at room temperature for 2.5 h
  3. filtrationThe resulting solid was filtered
  4. washwashed with water until neutral
  5. customThe solid was dried

Sources & evidence

ORD record
ord-89382b2e3e074ee5b12855cb87184aca
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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