Water → HCID 59401376, compound

Participants

Reaction Conditions

Reaction Steps

To 4-chloroquinoline-8-carbonitrile (Preparation 88) (422 mg 2.24 mmol) in toluene (20 mL) at −78° C. was added dropwise DIBAL-H (6.73 mL/1M solution in toluene, 6.73 mmol). After 20 min at −78° C. the mixture was allowed to warm to −40° C. The reaction mixture was then re-cooled to −78° C. and DIBAL-H (2.0 mL/1M solution in toluene, 2.0 mmol) was added. After 1 h water (1 mL), MeOH (5 mL) and then NH4Cl(aq) (10 mL) were added. After addition of EtOAc (20 mL) the mixture was stirred vigorously for 14 h at rt. The mixture was extracted with EtOAc (3×20 mL) and the combined organic phase washed with brine (20 mL) and dried (MgSO4). Solvent removed in vacuo to give the title compound: RT=2.10 min; m/z (ES+)=193.0 [M+H]+.

Provenance & Evidence