Acetic Acid → HCID 11687479, compound

HRID 884671Notes

Reaction equation

HRID 884671 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[C:10]1[O:11][C:12]2[C:17]([C:18](=[O:20])[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.I.C(O)(=O)C>O>[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:10]1[O:11][C:12]2[C:17]([C:18](=[O:20])[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24841Hydrogen iodideHCID 11543545HCID 11543545, compound

Product 1

HCID 11687479HCID 11687479, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer was added 2-(2-amino-4-methoxyphenyl)-4H-chromen-4-one (770 mg, 2.88 mmol), hydroiodic acid (10 mL) and acetic acid (4 mL). The reaction mixture was heated to 110° C. for 8 h. The reaction mixture was cooled to rt and diluted with water. The precipitate was filtered off, washed with water and dried to give the crude compound, which was purified by column chromatography using 2% MeOH in CH2Cl2, to give 2-(2-amino-4-hydroxy-phenyl)-chromen-4-one (357 mg, 49%). MS (ES) m/z: 254.05 (M+1), 149.00, 134.01, and 121.00.

Workup

  1. customTo a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customto give the crude compound, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7c0ab17e1be44d03b4f8f3c5c1517bd7
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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