Water → HCID 178509551, compound

HRID 870532Notes

Reaction equation

HRID 870532 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C([N-]C(C)C)(C)C.[Li+].[C:19](#[N:28])[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.O>O1CCCC1.O1CCCC1.CCCCCCC.C(C1C=CC=CC=1)C>[C:24]([C:23]1[CH:26]=[CH:27][C:20]([C:19]2[N:28]=[C:4]([OH:6])[C:3]3[CH:7]=[CH:8][CH:9]=[N:10][C:2]=3[CH:1]=2)=[CH:21][CH:22]=1)#[N:25]

Participants

7

Reactant 4

HCID 962WaterHCID 121721,4-DicyanobenzeneHCID 6433732-Methylnicotinic acidHCID 2724682Lithium diisopropylamide

Product 1

HCID 178509551HCID 178509551, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Conditions

Temperature
-78 °C

Procedure

1 g 2-methyl-nicotinic acid was suspended in 30 mL of tetrahydrofuran and cooled to −78° C. under nitrogen before 14.6 mL lithium diisopropylamide (as a 2.0 M in tetrahydrofuran/n-heptane/ethylbenzene) was added dropwise and the mixture was stirred for 2 h at −78° C. and then warmed to ambient temperature where it was maintained for a further 2 h. After this time the mixture was cooled to −78° C. and it was added dropwise into a solution of 1.87 g terephthalonitrile (4.33) in 30 mL tetrahydrofuran. The reaction mixture was stirred for 2 h and then warmed to ambient temperature overnight. After this time 20 mL water was added and the solvent was removed under reduced pressure before 20 mL ethyl acetate was introduced and the precipitate that was formed was collected by filtration. The solid material that was collected (title compound) was used without further purification.

Workup

  1. additionwas added dropwise
  2. temperaturewarmed to ambient temperature where it
  3. temperaturewas maintained for a further 2 h
  4. temperatureAfter this time the mixture was cooled to −78° C.
  5. stirringThe reaction mixture was stirred for 2 h
  6. temperaturewarmed to ambient temperature overnight
  7. customthe solvent was removed under reduced pressure before 20 mL ethyl acetate
  8. additionwas introduced
  9. customthe precipitate that was formed
  10. filtrationwas collected by filtration
  11. customThe solid material that was collected (title compound)
  12. customwas used without further purification

Sources & evidence

ORD record
ord-d0b782c119b443238165727143d7b6cb
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Reaction notes

Loading…