Fumaric Acid → 1000160-87-1

HRID 218333Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:6]2)[CH3:2].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>CO>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH2:12]([C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[CH2:1][CH3:2])[CH2:6][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:8]2)[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 2.208 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (5.625 mmoles) in 20 ml methanol is heated to 50° C. A solution of 0.326 g fumaric acid (2.81 mmoles) in 5 ml methanol is dropwise added to the suspension at constant flow rate, over 10 minutes. The resulting solution is stirred at 50° C. Crystallization takes then spontaneously place after ca. 10 minutes. The suspension is allowed to cool and stirred for 3 hours at room temperature. The mixture is filtered. The crystals are washed with 7 ml methanol and dried first for 20 hours at 60° C. and ca. 10 mbar and further for 2 h at 60° C. and ca. 1 mbar. Yield: 2.19 g white powder (86.4%)

Workup

customCrystallization
temperatureto cool
stirringstirred for 3 hours at room temperature
filtrationThe mixture is filtered
washThe crystals are washed with 7 ml methanol
customdried first for 20 hours at 60° C.
waitca. 10 mbar and further for 2 h at 60° C.

Sources & evidence

ORD record: ord-7ffa1c8d1106486fb84b59d6ef2ef108
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198450B2

Reaction notes

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