Aniline → 8-methoxy-2-oxo-N-phenyl-2H-chromene-3-carboxamide

HRID 240018Notes

Reaction equation

HRID 240018 reaction equation
CCN(C(C)C)C(C)C.CO[C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[C:17]([C:23]([OH:25])=O)[C:18](=[O:22])[O:19]2)=[CH:14][CH:13]=1.CN([C:29]([O:33]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C)C=O>[C:51]1([NH:50][C:23]([C:17]2[C:18](=[O:22])[O:19][C:20]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:21]=3[O:33][CH3:29])=[O:25])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 5839417-Methoxycoumarin-3-carboxylic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 7548218-methoxy-2-oxo-N-phenyl-2H-chromene-3-carboxamideYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.044 mL, 0.25 mmol) was added to 7-methoxy-3-carboxy-coumarin (0.050 g, 0.23 mmol) and HATU (0.095 g, 0.25 mmol) in 1 mL of dimethylformamide (DMF) with constant stirring at room temperature until a clear solution resulted. Subsequently, aniline (0.021 g, 0.23 mmol) was added and allowed to react overnight, when a yellow solid precipitated out of solution. The precipitate was filtered and dried under suction and then in vacuo to give 0.055 g of 1541H in an 82% yield: LCMS (ESI) m/z 296 (MH+).

Workup

  1. customresulted
  2. customto react overnight
  3. customwhen a yellow solid precipitated out of solution
  4. filtrationThe precipitate was filtered
  5. customdried under suction
  6. customin vacuo to give 0.055 g of 1541H in an 82% yield

Sources & evidence

ORD record
ord-d08b5c7c7d53475685514d9256aefd66
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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