Coumarin → 3-Aminocoumarin

HRID 523341Notes

Reaction equation

HRID 523341 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]1=[O:3].C([NH2:18])CCCCC.C1CCN2C(=NCCC2)CC1>>[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH2:18])[C:2]1=[O:3]

Participants

4

Reactant 3

HCID 323CoumarinHCID 8102HexylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 742173-Aminocoumarin

Procedure

Coumarin (0.3775 g, 2.583 mmol), 2.0 equimolar of n-hexylamine (0.5324 g, 5.261 mmol) and 0.1 equimolar of DBU (0.0418 g, 0.275 mmol) were added and mixed in bulk. The mixture was reacted in an oven and kept at 50° C. for 10 days. The resultant crude mixture was separated by preparative Thin Layer Chromatography (TLC) (eluent: ethylacetate/n-hexane=1/4 (vol./vol.)) to give corresponding coumarin monoamine (1:2) adduct (0.8287 g, 2.378 mmol, yield=92%).

Workup

  1. additionmixed in bulk
  2. customThe mixture was reacted in an oven
  3. customThe resultant crude mixture was separated by preparative Thin Layer Chromatography (TLC) (eluent: ethylacetate/n-hexane=1/4 (vol./vol.))

Sources & evidence

ORD record
ord-d57491d4334047e29a36b0581f8e6a68
Source dataset
uspto-grants-2016_05
Patent number
US09334426B2

Reaction notes

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