Hydrochloric Acid → HCID 9856743, compound

HRID 1765395Notes

Reaction equation

HRID 1765395 reaction equation
[F:1][C:2]1[C:7]2[C:8](=[O:20])[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=3)=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:21]C)[CH:3]=1.Cl.N1C=CC=CC=1.Cl>>[F:1][C:2]1[C:7]2[C:8](=[O:20])[C:9]([C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 21107100HCID 21107100, compound

Product 1

HCID 9856743HCID 9856743, compoundYield 68.5%

Conditions

Temperature
200 °C

Procedure

A mixture of 5-fluoro-7-methoxy-3-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran (132 mg) and pyridine hydrochloride (2 g) in a test tube was heated in an oil bath (preheated at 200° C.). The mixture melted, was stirred at 200° C. for 40 min and cooled. The residue was poured into 1N hydrochloric acid. The solids were filtered, washed with water and ether, and dried under high vacuum to give the title compound as a beige powder (82 mg). 1H NMR (DMSO-d6): 11.19 (s br, 1H), 9.55 (s br, 1H); 8.22 (s, 1H), 7.33 (d, 2H, J=7.8 Hz), 6.80 (d, 2H, J=7.8 Hz), 6.71 (s br, 1H), 6.65 (d br, 1H, J=12.9 Hz); MS: 273 (MH+); HPLC tR: 1.66 min.

Workup

  1. temperaturecooled
  2. filtrationThe solids were filtered
  3. washwashed with water and ether
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-7606a336bff74380b028691ee8146dd6
Source dataset
uspto-grants-2007_06
Patent number
US07226945B2

Reaction notes

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