Hydrochloric Acid → HCID 178468307, compound

HRID 1895201Notes

Reaction equation

HRID 1895201 reaction equation
[N:1]([O-])=O.[Na+].[F:5][C:6]1([F:16])[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([NH2:15])[C:8]=2[O:7]1.Cl.[CH3:18][C:19](=[O:24])[CH2:20][C:21](=[O:23])[CH3:22].C([O-])(=O)C.[Na+]>O.CO>[F:16][C:6]1([F:5])[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([NH:15][N:1]=[C:20]([C:19](=[O:24])[CH3:18])[C:21](=[O:23])[CH3:22])[C:8]=2[O:7]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 27368912,2-Difluoro-1,3-dioxaindan-4-amineHCID 23668193Sodium Nitrite

Product 1

HCID 178468307HCID 178468307, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium nitrite (0.96 g, 14 mmol) in H2O (5 mL) was added dropwise to a solution of 2,2-difluoro-1,3-benzodioxol-4-amine (2.0 g, 12 mmol) in 6 M HCl aqueous solution (12 mL, 72 mmol) at 0° C. After stirring for 15 min at 0° C., the mixture was added to a suspension of 2,4-pentanedione (1.2 mL, 12 mmol) and sodium acetate (5.9 g, 72 mmol) in MeOH (20 mL) pre-cooled at 0° C. The formed precipitate was collected by filtration, washed with water and dissolved in AcOEt. The organic solution was washed with saturated NaHCO3 aqueous solution and brine, dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (3.0 g, 90% yield) as orange crystals: 1H NMR (300 MHz, CDCl3): δ ppm 2.49 (3H, s), 2.63 (3H, s), 6.88 (1H, dd, J=8.0, 1.1 Hz), 7.13 (1H, t, J=8.1 Hz), 7.30 (1H, dd, J=8.5, 1.1 Hz), 14.56 (1H, brs).

Workup

  1. temperaturepre-cooled at 0° C
  2. filtrationThe formed precipitate was collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in AcOEt
  5. washThe organic solution was washed with saturated NaHCO3 aqueous solution and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70b7eff6b748413d858e9653218ea98f
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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