Calcium Carbonate → 3-((3-Hydroxypropyl)methylamino)benzonitrile

Reaction equation

[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].Cl[CH2:12][CH2:13][CH2:14][OH:15].C([O-])([O-])=O.[Ca+2]>O>[OH:15][CH2:14][CH2:13][CH2:12][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

Procedure

3-methylaminobenzonitrile (17.34 g, 0.13 mol, 1.0 eq), 3-chloropropanol (49.70 g, 0.53 mol, 4.0 eq) and CaCO3 (52.50 g, 0.53 mol, 4.0 eq) are added into water (230 ml) at room temperature, the mixture is refluxed at elevated temperature for 40 h, and cooled, filtered and extracted with ethyl acetate (200 ml*3). The organic phases are combined, washed with water (100 ml*2), washed with saturated brine twice, dried over anhydrous sodium sulfate and concentrated to give a light yellow oily crude product (31.08 g). The residue could be used directly in next step without purification.