2-Fluorobenzonitrile → HCID 12487883, compound

HRID 919172Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[Li]CCCC.[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>>[C:10]([C:9]1[N:24]=[C:23]([C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[F:20])[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=2)[N:8]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

Reactant 3

HCID 678552-Fluorobenzonitrile

HCID 182511Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-

HCID 178418339Butyllithium

Product 1

HCID 12487883HCID 12487883, compoundYield 57%

Procedure

The preparation of 4-phenylquinazolines from amidobenzenes or benzonitriles, as shown in the reaction when p-chloropivalamidobenzene was dilithiated with n-BuLi followed by the addition of o-fluorobenzonitrile to give 57% of 2-t-butyl-6-chloro-4-o-fluorophenylquinazoline [26], and the treatment of o-aminobenzonitrile with phenylmagnesium halide from which the resulting intermediate 2-H2NC6H4C(Ph)=N− then cyclized with carbonyl compounds (e.g., acid chlorides, anhydrides, formates) to give 4-phenyl-quinazolines [27]. Alternatively, the reaction between benzanilides and benzonitriles in the presence of PCl5 and AlCl3 in PhNO2 at 120-150° C. also afforded 2,4-diphenylquinazoline [28];

Sources & evidence

ORD record: ord-3a10feb706244c25a412773aa7fd7afe
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273012B2

Reaction notes

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