Triethylamine → HCID 178439761, compound

HRID 522365Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.C(O[CH2:24][CH:25]=[CH2:26])(=O)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:26]([C:11]1[C:2]([OH:1])=[N:3][C:4]2[C:9]([C:10]=1[OH:12])=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:25]=[CH2:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a degassed solution of 2,4-dihydroxyquinoline (10.0 g) in DMF (100 ml) was added triethylamine (9.51 ml), Pd(Ph3P)4 (2.151 g), followed by allyl acetate (7.43 ml). The mixture was allowed to stir at 60° C. under nitrogen for 18 hours. The reaction mixture was cooled to room temperature and quenched into water (600 mL). The pH was adjusted to 12 using a saturated sodium carbonate solution. Dichloromethane was added and the layers were cut. The aqueous layer was extracted with dichloromethane once more. Then, the aqueous layer was cooled with ice and the pH was slowly adjusted to 2.5 with 12N HCl to give a pink solid. The solids were filtered and washed with water to give 11.5 g (92% yield). LRMS (ES+) M/Z (M+H)+ 202.0.

Workup

temperatureThe reaction mixture was cooled to room temperature
customquenched into water (600 mL)
additionDichloromethane was added
extractionThe aqueous layer was extracted with dichloromethane once more
temperatureThen, the aqueous layer was cooled with ice
customto give a pink solid
filtrationThe solids were filtered
washwashed with water
customto give 11.5 g (92% yield)

Sources & evidence

ORD record: ord-ea9ea43f0b164877a836ade3f8d36bc7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328138B2

Reaction notes

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