Nitric Acid → HCID 58368547, compound

HRID 1192512Notes

Reaction equation

HRID 1192512 reaction equation
[Cl:1][C:2]1[C:3]([C:13]#[C:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[N+:19]([O-])([OH:21])=[O:20].O>C(O)(=O)C>[Cl:1][C:2]1[C:3]([C:13]#[C:14][Si:15]([CH3:16])([CH3:18])[CH3:17])=[C:4]([N+:19]([O-:21])=[O:20])[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 962WaterHCID 58368507HCID 58368507, compound

Product 1

HCID 58368547HCID 58368547, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
55 °C

Procedure

A solution of methyl 5-chloro-2-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate (15 g, 53 mmol) in acetic acid (110 mL) at 55° C. was treated with a solution of nitric acid (7.8 mL, 190 mmol) in acetic acid (7.8 mL, 140 mmol) dropwise and stirred at 55° C. for 30 minutes. The reaction mixture contained only starting material and was treated with an additional solution of nitric acid (2.2 mL, 53 mmol) in acetic acid (2.2 mL, 39 mmol) dropwise and stirred at 55° C. for 1.5 hour. The reaction mixture was cooled to 0° C. and treated with ice followed by cold water. The reaction mixture was stirred until the ice melted, filtered, washed with cold water, and air dried to give the desired product (11.7 g, 67%) as a tan solid. This material was used without further purification. LCMS for C13H15ClNO5Si (M+H)+: m/z=328.0; Found: 327.8.

Workup

  1. stirringstirred at 55° C. for 1.5 hour
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. additiontreated with ice
  4. filtrationfiltered
  5. washwashed with cold water, and air
  6. customdried

Sources & evidence

ORD record
ord-181802e76982458f8b0ed58571ba0fda
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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