Ammonia → HCID 57983498, compound

HRID 1868906Notes

Reaction equation

HRID 1868906 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15](OCC)=[O:16])=[C:5]2[OH:20].[NH3:21]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH2:21])=[O:16])=[C:5]2[OH:20]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 67099655HCID 67099655, compound

Product 1

HCID 57983498HCID 57983498, compoundYield 2.9%

Conditions

Temperature
70 °C

Procedure

Ethyl 6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (1.19 g, 4038 μmol, see Example 2) was dissolved in ammonia (0.5M in 1,4-dioxane (40376 μL, 20188 μmol)), and the resulting mixture was heated at 70° C. for 16 hours. The reaction mixture was then concentrated, dissolved in MeOH and ammonium hydroxide, and stirred at ambient temperature for 16 hours. The reaction mixture was then heated at 80° C. for 16 hours. The reaction mixture was concentrated, suspended in DCM, filtered, and washed with DCM. The mother liquor was purified via preparatory LC to give the title compound (31 mg) as an off-white solid. MS m/e=266 (M+H)+. Calculated for C13H12ClNO3 265.09.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutiondissolved in MeOH
  3. temperatureThe reaction mixture was then heated at 80° C. for 16 hours
  4. concentrationThe reaction mixture was concentrated
  5. filtrationfiltered
  6. washwashed with DCM
  7. customThe mother liquor was purified via preparatory LC

Sources & evidence

ORD record
ord-8514ff650099456f8375f26b45a1fb9a
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…