Water → 7-(3,4,5-Trimethoxyphenyl)quinolin-5-ol

HRID 1402706Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]2[C:20]([C:21](=[O:23])[CH3:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[OH-].[Na+].O.OS([O-])(=O)=O.[K+]>S(=O)(=O)(O)O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[CH:22]=[C:21]([OH:23])[C:20]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3[CH:14]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 25 °C

Procedure

90 mg 1-(2-(3,4,5-trimethoxyphenylethynyl)pyridin-3-yl)ethanone were suspended in 750 μL 1N sulfuric acid and 4 mg mercuric chloride and stirred for 1 h 45 minutes at 60° C. Then 2 mL of NaOH was added and the mixture stirred for additional 1 h at 25° C. Water was added and a neutral pH was adjusted with KHSO4 solution. The precipitate was filtered off and washed with water and dried to yield 80 mg 7-(3,4,5-trimethoxyphenyl)quinolin-5-ol 6.2 as solid. Analysis: HPLC-MS: Rt=1.18 min (method D), M+H=330.

Workup

filtrationThe precipitate was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-7137a38a35b94c61ae39eb9431740717
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912173B2

Reaction notes

Loading…