Acetic Acid → HCID 178486760, compound

HRID 548475Notes

Reaction equation

C([Li])CCC.[C:6](#[N:8])[CH3:7].[CH2:9]([O:16][C:17]1[C:26]([O:27][CH3:28])=[CH:25][C:20]([C:21]([O:23]C)=O)=[C:19]([N:29]=[CH:30]N(C)C)[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C>C1COCC1>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]2[C:20]([C:21]([OH:23])=[C:7]([C:6]#[N:8])[CH:30]=[N:29]2)=[CH:25][C:26]=1[O:27][CH3:28])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 26.9 ml of n-butyllithium (2.5 M in hexane) in 50 ml of THF at −78° C. was added a 3.51 ml of acetonitrile in 20 ml of THF during 10 min. After stirring at −78° C. for 30 min, the mixture was treated with 10 g of methyl 4-benzyloxy-2-(dimethylaminomethyleneamino)-5-methoxybenzoate in 20 ml of THF during 5 min. After 15 min at −78° C. the stirred mixture was warmed to 0° C. for a further 30 min. It was then treated with 5 ml of acetic acid, warmed to 25° C. and stirred for 30 min. The mixture was evaporated to dryness, and diluted with aqueous sodium bicarbonate. The resulting off-white solid was filtered, washed with water, ethyl acetate and ether. After drying, 4.5 g of 7-benzyloxy-4-hydroxy-6-methoxy-quinoline-3-carbonitrile was obtained as an off-white solid, dec >255° C.; mass spectrum (electrospray, m/e) M+H 307.

Workup

temperatureAfter 15 min at −78° C. the stirred mixture was warmed to 0° C. for a further 30 min
temperaturewarmed to 25° C.
stirringstirred for 30 min
customThe mixture was evaporated to dryness
additiondiluted with aqueous sodium bicarbonate
filtrationThe resulting off-white solid was filtered
washwashed with water, ethyl acetate and ether
customAfter drying

Sources & evidence

ORD record: ord-93d5e2bf193141c48da9af3d106bbcd4
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE042376E1

Reaction notes

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