Pyridine → HCID 20400421, compound

HRID 1981244Notes

Reaction equation

HRID 1981244 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[C:8]([CH3:13])[O:9]2)=[CH:4][CH:3]=1.CN(C)[CH:20]=[O:21].N1C=CC=C[CH:24]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C(OCC)(=O)C>[C:29]([O:1][C:2]1[C:11]([O:12][C:20](=[O:21])[CH3:24])=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[C:8]([CH3:13])[O:9]2)=[CH:4][CH:3]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 20400419HCID 20400419, compound

Product 1

HCID 20400421HCID 20400421, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7,8-dihydroxy-2-methylchromone-3-carboxylic acid (0.9 g), dimethylformamide (10 ml), pyridine (0.92 ml) and acetic anhydride (1.2 ml) was stirred at room temperature for 4 hours. Ethyl acetate (100 ml) was added to the liquid reaction mixture, and the organic layer was washed successively with 6N-HCl and water, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and ethyl ether was added to the residue. The resulting solid was collected by filtration and then washed with a 1:1 mixed solvent of ethyl acetate and ethyl ether, followed by drying to afford the desired product (0.534 g).

Workup

  1. washthe organic layer was washed successively with 6N-HCl and water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. additionethyl ether was added to the residue
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with a 1:1 mixed solvent of ethyl acetate and ethyl ether
  7. customby drying

Sources & evidence

ORD record
ord-18af5f3bdc3a4a388e536421befdd7d5
Source dataset
uspto-grants-1985_04
Patent number
US04513145

Reaction notes

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