Ammonia → HCID 57983498, compound

HRID 2078314Notes

Reaction equation

HRID 2078314 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-0b31d2ec33444c88851affa641376044
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

Loading…