3,4,5-Trimethoxybenzonitrile → HCID 178487380, compound

HRID 870531

Reaction equation

HRID 870531 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(O)C.C(=O)=O.C([N-]C(C)C)(C)C.[Li+].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:30]#[N:31]>O1CCCC1.O>[CH3:38][O:37][C:33]1[CH:32]=[C:29]([C:30]2[N:31]=[C:4]([OH:6])[C:3]3[CH:7]=[CH:8][CH:9]=[N:10][C:2]=3[CH:1]=2)[CH:28]=[C:27]([O:26][CH3:25])[C:34]=1[O:35][CH3:36]

Participants

7

Reactant 4

HCID 158923,4,5-TrimethoxybenzonitrileHCID 6433732-Methylnicotinic acidHCID 2724682Lithium diisopropylamideHCID 19604758Methanedione--ethanol (1/1)

Product 1

HCID 178487380HCID 178487380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

7 g 2-Methyl-nicotinic acid was suspended in 150 mL of tetrahydrofuran, and cooled to −70° C. with a bath of ethanol/dry ice. 80 mL lithium diisopropylamide (2.0 M in tetrahydrofuran/n-heptane/ethylbenzene) was added dropwise over 10 min and the mixture was stirred for 2 h at 0° C. Then it was cooled to −73° C. and a solution of 10 g 3,4,5-trimethoxy-benzonitrile (4.24) in 50 mL tetrahydrofuran was added. Then the reaction mixture was warmed overnight to ambient temperature. 30 mL Water was added and the solvent was distilled off before 200 mL ethyl acetate was added and the precipitate that formed was collected.

Workup

  1. temperatureThen it was cooled to −73° C.
  2. temperatureThen the reaction mixture was warmed overnight to ambient temperature
  3. distillationthe solvent was distilled off before 200 mL ethyl acetate
  4. additionwas added
  5. customthe precipitate that formed
  6. customwas collected

Sources & evidence

ORD record
ord-78e6103bd710448bb48c3fe0d82c9112
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Linked notes

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