Ammonia → HCID 49864197, compound

HRID 250786Notes

Reaction equation

HRID 250786 reaction equation
Cl.C([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:10]([OH:22])[C:9]2=[O:23])(=O)C.N>C(O)C>[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:10]([OH:22])[C:9]2=[O:23]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 49864161N-(3-hydroxy-4-oxo-2-phenyl-chromen-6-yl)acetamide

Product 1

HCID 49864197HCID 49864197, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous HCl (5 M, 20 mL) was added to a suspension of 6-acetamidoflavonol (6) (1.00 g, 3.39 mmol) in ethanol (30 mL) and the mixture was heated under reflux for 1.5 h. The mixture was cooled and made basic with aqueous NH3 (litmus) and the precipitate formed was collected by filtration to afford 6-aminoflavonol as a bright yellow powder (0.437 g, 51%), m.p. 211-212° C. 1H NMR (399.7 MHz, d6-DMSO) δ 5.48 (s, 1H, NH); 7.08 (dd, 1H, J5,7 2.8, J7,8 9.2 Hz, H7); 7.14 (d, 1H, J5,7 2.8 Hz, H5); 7.47-7.57 (m, 4H, H3′,4′,5′,8); 8.17 (app. d, 2H, J=7.6 Hz, H2′,6′); 8.62 (br s, 1H, OH).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 h
  3. temperatureThe mixture was cooled
  4. customthe precipitate formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-14ffec058f2e4ae683ba8f6cd8e7db05
Source dataset
uspto-grants-2011_01
Patent number
US07863323B1

Reaction notes

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