Acetic Acid → HCID 178510317, compound

HRID 347442Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[OH:13])=[C:10](F)[CH:9]=[C:8]([F:15])[CH:7]=2)#[N:2].[O:16]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]1.CC(C)([O-])C.[K+].C(O)(=O)C>O1CCCC1>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[OH:13])=[C:10]([O:22][CH:19]1[CH2:20][CH2:21][O:16][CH2:17][CH2:18]1)[CH:9]=[C:8]([F:15])[CH:7]=2)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-cyano-5,7-difluoro-4-hydroxyquinoline (2.06 g), tetrahydro-2H-pyran-4-ol (1.02 g) and potassium tert-butoxide (1.0M solution in tetrahydrofuran; 30.0 ml) in anhydrous tetrahydrofuran (100 ml) was stirred and heated under nitrogen at 60° C. for 1.5 hours. Acetic acid was added until pH6 was reached and then the solution was evaporated to dryness. The residue was dissolved in aqueous sodium hydroxide solution (2.0M) and the resulting solution was filtered through a GF/A glass fibre pad. The filtrate was acidified to pH5 with acetic acid and the resulting oily precipitate allowed to stand 3 days when it had become solid. The solid was collected and washed with water then air-dried. (1.8 g, 62%); NMR spectrum: (DMSOd6) 1.67 (m, 2H), 1.92 (m, 2H), 3.50 (m, 2H), 3.91 (m, 2H), 4.76 (m, 1H), 6.81 (m, 1H), 6.94 (m, 1H), 8.52 (s, 1H); Mass spectrum: M+H+ 289.

Workup

customthe solution was evaporated to dryness
dissolutionThe residue was dissolved in aqueous sodium hydroxide solution (2.0M)
filtrationthe resulting solution was filtered through a GF/A glass fibre pad
customThe solid was collected
washwashed with water
customthen air-dried

Sources & evidence

ORD record: ord-f5fc14c45af14cb0b50d926f45c9dea0
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173135B2

Reaction notes

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