Thionyl Chloride → Methyl 5-cyano-2-methoxybenzoate

HRID 391401Notes

Reaction equation

HRID 391401 reaction equation
O[N:2]=[CH:3][C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10].S(Cl)(Cl)=O>C(Cl)Cl>[C:3]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])#[N:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58993456Methyl 5-[(hydroxyimino)methyl]-2-methoxybenzoate

Product 1

HCID 18464789Methyl 5-cyano-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 5-((hydroxyimino)methyl)-2-methoxybenzoate (1.04 g, 4.94 mmol) was dissolved in methylene chloride (25 mL) and cooled to 0° C. The reaction was treated with thionyl chloride (0.59 mL, 8.1 mmol) and stirred at 0° C. for 2 h. After warming to room temperature, the reaction was diluted with methylene chloride, washed with saturated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated to afford 0.87 g (92%) which was used without further purification. 1H-NMR (CDCl3, 500 MHz) δ 8.09 (d, J=2.1 Hz, 1H), 7.75 (dd, J=8.9, 2.1 Hz, 1H), 7.05 (d, J=8.9 Hz, 1H), 3.96 (s, 3H), 3.90 (s, 3H). Mass spec.: 192.02 (MH)+.

Workup

  1. temperatureAfter warming to room temperature
  2. washwashed with saturated sodium bicarbonate (2×), brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto afford 0.87 g (92%) which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-33f75a249c0d4affa0af19ca048c83bd
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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