Water → 4-(6-Hydroxyquinolin-2-yl)benzonitrile

HRID 1507341Notes

Reaction equation

HRID 1507341 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].O1CCOCC1.O>CCOC(C)=O>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:18]1[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=1)[CH:11]=[CH:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 27343264-Cyanophenylboronic acidHCID 221325772-Chloroquinolin-6-ol2×

Product 1

HCID 669800944-(6-Hydroxyquinolin-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Followed Scheme 3 starting from 2-chloroquinolin-6-ol (Intermediate 2) and 4-cyanophenylboronic acid, and using 1,4-Dioxane:H2O solution. Reaction was run at 100° C. in a microwave reactor for 1 hour. Ethyl acetate workup was followed by column chromatography (5% to 50% EtOAc in hexanes gradient).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-a55ecb8384b94152bb41318152378e46
Source dataset
uspto-grants-2015_12
Patent number
US09221810B2

Reaction notes

Loading…