Hydrochloric Acid → HCID 178468349, compound

HRID 1747761Notes

Reaction equation

HRID 1747761 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)[CH:6]=[CH:5][C:3]=1[NH2:4].Cl.[N:15]([O-])=O.[Na+].[Br:19][C:20]1[CH:24]=[CH:23][O:22][C:21]=1[C:25](=[O:30])[CH2:26][C:27](=[O:29])[CH3:28].C([O-])(=O)C.[Na+]>O.CO>[Br:19][C:20]1[CH:24]=[CH:23][O:22][C:21]=1[C:25](=[O:30])[C:26](=[N:15][NH:4][C:3]1[CH:5]=[CH:6][C:7]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:8][C:2]=1[F:1])[C:27](=[O:29])[CH3:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 57471888HCID 57471888, compoundHCID 89586109HCID 89586109, compound

Product 1

HCID 178468349HCID 178468349, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 2-fluoro-4-(1H-pyrazol-1-yl)aniline (2.3 g) and 6M hydrochloric acid (13 mL) was added dropwise a solution of sodium nitrite (1.0 g) in water (3 mL) at 0° C., and the mixture was stirred for 15 min. The obtained aqueous solution was added to a suspension, which was cooled to 0° C., of 1-(3-bromofuran-2-yl)butane-1,3-dione (3 g) and sodium acetate (6.4 g) in methanol (30 mL). The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (5.3 g).

Workup

  1. additionThe obtained aqueous solution was added to a suspension, which
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32eb5da7735f47c1862387d2b2fe3bc6
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

Loading…