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2,2-Dimethyl-1,3-dioxane-4,6-dione → 8-(4-Morpholinylmethyl)-3-carboxy-6-methoxy-coumarin

HRID 240014
Notes
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Reaction equation

HRID 240014 reaction equation
[OH:1][C:2]1[C:9]([CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:8][C:7]([O:17][CH3:18])=[CH:6][C:3]=1[CH:4]=O.CC1(C)O[C:25](=[O:26])[CH2:24][C:22](=[O:23])[O:21]1>O>[N:11]1([CH2:10][C:9]2[CH:8]=[C:7]([O:17][CH3:18])[CH:6]=[C:3]3[C:2]=2[O:1][C:25](=[O:26])[C:24]([C:22]([OH:23])=[O:21])=[CH:4]3)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 450543922-Hydroxy-5-methoxy-3-(4-morpholinylmethyl)benzaldehyde

Product 1

HCID 866503618-(4-Morpholinylmethyl)-3-carboxy-6-methoxy-coumarinYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

2-hydroxy-5-methoxy-3-(4-morpholinylmethyl)benzaldehyde (0.349 g, 1.39 mmol) and Meldrum's acid (0.200 g, 1.39 mmol) were combined in H2O (2 mL). The solution was stirred at 75° C. for 2 h. After cooling to room temperature, the precipitate was filtered and dried at suction to give 0.381 g of 8-(4-morpholinylmethyl)-3-carboxy-6-methoxy-coumarin in an 85% yield: LCMS (ESI) m/z 320 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered
  3. customdried at suction

Sources & evidence

ORD record
ord-2c7d7887828c41da88803e00485bce84
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642788B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes