Dimethylformamide → HCID 178429078, compound

Reaction equation

[Cl:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6](Cl)[C:3]=1[C:4]#[N:5].CN(C)C=[O:15]>>[Cl:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([OH:15])[C:3]=1[C:4]#[N:5]

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 112754712,4-Dichloro-6-methylnicotinonitrile

Product 1

HCID 178429078HCID 178429078, compoundYield 84.1%

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,4-dichloro-6-methylnicotinonitrile (12.0 g, 64.2 mmol), CsOAc (37.0 g, 193.0 mmol) in N,N-dimethylformamide (50 mL) was stirred at 80° C. overnight under N2. The mixture was partitioned between water (800 mL) and ethyl acetate (800 mL), the organic layer was dried and concentrated to afford 2-chloro-4-hydroxy-6-methylnicotinonitrile (9.0 g brown solid, 84.1% yield).

Workup

customThe mixture was partitioned between water (800 mL) and ethyl acetate (800 mL)
customthe organic layer was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-3c901f2f004b4ee2ae35ffa56c9537b0
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085583B2

Reaction notes

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