4-Aminobenzonitrile → 4-{[Cyano(2-fluoro-3-hydroxy-5-methoxyphenyl)methyl]amino}benzonitrile

HRID 2089678Notes

Reaction equation

[F:1][C:2]1[C:9]([OH:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=O.[NH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C[Si]([C:26]#[N:27])(C)C.C(=O)([O-])O.[Na+]>CO.Cl.NC(N)=N>[C:26]([CH:4]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)[C:3]1[CH:6]=[C:7]([O:11][CH3:12])[CH:8]=[C:9]([OH:10])[C:2]=1[F:1])#[N:27]

Participants

Conditions

Temperature: 40 °C

Procedure

Under nitrogen atmosphere, a solution of 2-fluoro-3-hydroxy-5-methoxybenzaldehyde (17.01 g, 100 mmol), 4-aminobenzonitrile (11.81 g, 100 mmol), and guanidine hydrochloride (287 mg, 3 mmol) in methanol (85 mL) was stirred at 40° C. for 1.5 hours. Trimethylsilylcyanide (18.1 mL, 130 mmol) was then added dropwise thereto, and the resulting mixture was stirred at 40° C. for 22 hours. After cooling the mixture, under cooling at 15° C., 3% aqueous sodium hydrogen carbonate solution (87.65 g) was added dropwise thereto, and the resulting mixture was stirred for 1 hour under cooling at 10° C. The precipitated solid was filtered and dried to obtain the captioned compound (27.91 g) as a white solid.

Workup

temperatureAfter cooling the mixture
temperatureunder cooling at 15° C.
stirringthe resulting mixture was stirred for 1 hour
temperatureunder cooling at 10° C
filtrationThe precipitated solid was filtered
customdried

Sources & evidence

ORD record: ord-1b2f7d66405c4f43acc7030397091728
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436009B2

Reaction notes

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