Hydrochloric Acid → HCID 57729249, compound

HRID 1988194Notes

Reaction equation

HRID 1988194 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([C:19]([O:21]C)=[O:20])=[C:15]([CH3:18])[CH:16]=3)[O:11][C:10](=[O:23])[CH:9]=2)=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([C:19]([OH:21])=[O:20])=[C:15]([CH3:18])[CH:16]=3)[O:11][C:10](=[O:23])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57729261HCID 57729261, compound

Product 1

HCID 57729249HCID 57729249, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-2H-chromene-7-carboxylate (0.722 g, 2.31 mmol) in THF (23 mL) was added a 1 N solution of LiOH (11.6 mL, 11.6 mmol), and the mixture was heated at 65° C. for 16 h. At room temperature, the mixture was neutralized with 1 N HCl and concentrated. The residue was stirred with THF (25 mL) and 2 N HCl (50 mL) for 16 h. The precipitate produced was collected by filtration, rinsed with water and dried, affording the title compound that was used without further purification. 1H NMR (500 MHz, DMSO-d6): δ 13.40 (br s, 1H), 7.80 (s, 1H), 7.64 (m, 2H), 7.44 (m, 2H), 7.32 (s, 1H), 6.54 (s, 1H), 2.48 (s, 3H).

Workup

  1. customAt room temperature
  2. concentrationconcentrated
  3. customThe precipitate produced
  4. filtrationwas collected by filtration
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-077df45a1b8142918e317a5cc08b27d1
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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