4-isopropoxybenzonitrile → HCID 70978446, compound

HRID 1852251Notes

Reaction equation

HRID 1852251 reaction equation
C([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[CH3:13])C.[Li]CCCC.[CH:22]([O:25][C:26]1[CH:33]=[CH:32]C(C#N)=[CH:28][CH:27]=1)([CH3:24])[CH3:23]>C1COCC1>[CH:22]([O:25][C:26]1[CH:33]=[CH:32][C:16]([C:15]2[NH:3][C:4](=[O:14])[C:5]3[C:6]([CH:13]=2)=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=3)=[CH:28][CH:27]=1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 110082274-isopropoxybenzonitrileHCID 11053218N,N-diethyl-4-methoxy-2-methyl-benzamideHCID 178418339Butyllithium

Product 1

HCID 70978446HCID 70978446, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N,N-diethyl-4-methoxy-2-methylbenzamide (3.5 g, 15.82 mmol) in THF (35 ml) was added n-BuLi (2.82 ml, 4.52 mmol, in hexane) at −78° C. and stirred for 1 h. 4-isopropoxy benzonitrile (2.55 g, 15.82 mmol) was added at same temperature and allowed to warm to room temperature and continued the stirring for another 1 h at room temperature. The reaction mixture was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc (2*100 ml). The organic phase was washed with brine then dried on Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to get desired compound (3.5 g, 71.5%) as white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.21(s, 1H), 8.09-8.07 (d, J=8 Hz, 1H), 7.71-7.69 (d, J=8 Hz, 2H), 7.14 (d, J=8 Hz, 1H), 7.03-7.01 (d, J=8 Hz, 3H), 6.76 (s, 1H), 4.71 (m, 1H), 3.88 (s, 3H), 1.30 (m, 6H); MS: MS m/z 310.7 (M++1).

Workup

  1. customstirring for another 1 h
  2. customat room temperature
  3. customThe reaction mixture was quenched with saturated aqueous NH4Cl solution
  4. extractionextracted with EtOAc (2*100 ml)
  5. washThe organic phase was washed with brine
  6. customthen dried on Na2SO4
  7. customevaporated under reduced pressure
  8. customto get crude compound
  9. customThe crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-6f28c78d0409403b933ce13cba96a9d8
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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