Malonic Acid → HCID 24178421, compound

HRID 218343Notes

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:36])(=[O:35])[CH2:31][C:32]([OH:34])=[O:33]>C(O)CCC>[C:30]([OH:36])(=[O:35])[CH2:31][C:32]([OH:34])=[O:33].[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: 80 °C

Procedure

A suspension of 2.172 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (5.533 mmoles) und 0.576 g malonic acid (5.533 mmoles) in 25 ml n-butanol is heated to 80° C. Initially an oil formed during heating, which crystallizes on prolonged heating. The mixture is stirred at 80° C. for 15 minutes and then allowed to cool to room temperature. The suspension is stirred for 18 hours at room temperature. After filtration the crystals are washed with 5 ml n-butanol and 10 ml acetone. The product is dried at 70° C. and 70° C. for 20 hours. Yield: 2.62 g white powder (95.28%)

Workup

customInitially an oil formed
temperatureduring heating
customwhich crystallizes on prolonged heating
temperatureto cool to room temperature
stirringThe suspension is stirred for 18 hours at room temperature
filtrationAfter filtration the crystals
washare washed with 5 ml n-butanol and 10 ml acetone
customThe product is dried at 70° C. and 70° C. for 20 hours

Sources & evidence

ORD record: ord-03145cd7b1964f539f289936c965b836
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198450B2

Reaction notes

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