[NH2:1][C:2]1[C:3]([Cl:14])=[CH:4][C:5]([CH2:10][CH2:11][CH:12]=[O:13])=[C:6]([CH:9]=1)[C:7]#[N:8].C1COCC1.[BH4-].[Na+]>CO>[NH2:1][C:2]1[C:3]([Cl:14])=[CH:4][C:5]([CH2:10][CH2:11][CH2:12][OH:13])=[C:6]([CH:9]=1)[C:7]#[N:8]5-amino-4-chloro-2-(3-oxopropyl)benzonitrile (200 mg, 0.959 mmol) was taken up in MeOH (2 mL) and THF (2 mL) and cooled to 0° C. NaBH4 (54.4 mg, 1.438 mmol) was added, and the reaction was stirred at 0° C. for 6 h (reaction followed by TLC). The reaction was quenched with water and extracted 2× with DCM. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-50% EtOAc/DCM; 40 g column). 5-amino-4-chloro-2-(3-hydroxypropyl)benzonitrile (125 mg) was obtained as a yellow glass.
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