Hexamethylphosphoramide → Methyl 4-cyano-3-nitrobenzoate

HRID 1844783Notes

Reaction equation

HRID 1844783 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][N:16](C)P(=O)(N(C)C)N(C)C>>[C:15]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])#[N:16]

Participants

3

Reactant 2

HCID 12679HexamethylphosphoramideHCID 297884Methyl 4-iodo-3-nitrobenzoate

Product 1

HCID 53419688Methyl 4-cyano-3-nitrobenzoateYield 80.4%

Conditions

Temperature
100 °C

Procedure

5 g (0.016 mol) Methyl 4-iodo-3-nitrobenzoate (Compound IV-1), 1.77 g (0.02 mol) cuprous cyanide and 15 ml hexamethylphosphoric triamide were added into a reaction flask, and heated to 100° C. and reacted for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, then extracted with 100 ml ethyl acetate, and the organic layer was washed with water for three times, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness, separated by column chromatography to obtain methyl 4-cyano-3-nitrobenzoate (Compound II-8), 2.7 g (0.013 mol), yield 80.4%.

Workup

  1. customreacted for 1 hour
  2. temperaturethe mixture was cooled to room temperature
  3. extractionextracted with 100 ml ethyl acetate
  4. washthe organic layer was washed with water for three times
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to dryness
  8. customseparated by column chromatography

Sources & evidence

ORD record
ord-66f4b5b90a1a4a659c1917621c48b0d0
Source dataset
uspto-grants-2015_02
Patent number
US08946478B2

Reaction notes

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