Water → 7-Phenylquinolin-5-ol

HRID 1496857Notes

Reaction equation

[C:1]1([C:7]#[C:8][C:9]2[C:14]([C:15](=[O:17])[CH3:16])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[C:1]1([C:7]2[CH:16]=[C:15]([OH:17])[C:14]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Step 2 (=Reaction 2): 30 mg 1-(2-(Phenylethynyl)pyridin-3-yl)ethanone were suspended in 350 μL 1N sulfuric acid and 2.147 mg mercuric chloride and stirred for 30 min at 60° C. Then 1 mL of NaOH was added and the mixture stirred for additional 1 h at 25° C. Water was added and a neutral pH adjusted with NaHCO3 solution. The precipitate was filtered off and washed with water and dried to yield 30 mg 7-phenylquinolin-5-ol 6.1 as solid. Analysis: HPLC-MS: Rt=1.18 min (method D), M+H=240.

Workup

customStep 2 (=Reaction 2)
filtrationThe precipitate was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-0c5e40c0ea8c4268922836377a201087
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199937B2

Reaction notes

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