Hydrochloric Acid → HCID 59406908, compound

HRID 1948305Notes

Reaction equation

HRID 1948305 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[NH:6][C:7]([CH3:12])=[C:8]([F:11])[C:9]=1[F:10])=[O:4].[OH-:15].[Na+].Cl>>[F:10][C:9]1[C:8]([F:11])=[C:7]([CH3:12])[NH:6][C:5]=1[C:3]([OH:4])=[O:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68517068HCID 68517068, compound2×

Product 1

HCID 59406908HCID 59406908, compound

Procedure

2,2,2-Trichloro-1-(3,4-difluoro-5-methyl-1H-pyrrol-2-yl)ethanone (Intermediate 80; 1.03 g) was added to an aqueous solution of NaOH (18 ml) at 0° C. under N2. The mixture was stirred at room temperature for a further 2 h, cooled to 0° C. and acidified with HCl to ˜pH 2. A brown precipitate of product was collected by filtration. The crude product was purified by column chromatography on silica gel elution with EtOAc/hexanes (1:1). Trituration with DCM (1 ml)/pentane (6 ml) gave the title compound as a pale brown solid (306 mg). M.p. 140° C. (dec.). MS (ES) MH+: 160, 161 for C6H5F2NO2; NMR (CDCl3): 2.15 (s, 3H), 11.5 (s, 1H), 12.8 (brs, 1H).

Workup

  1. temperaturecooled to 0° C.
  2. filtrationA brown precipitate of product was collected by filtration
  3. customThe crude product was purified by column chromatography on silica gel elution with EtOAc/hexanes (1:1)

Sources & evidence

ORD record
ord-15022c9706cb4c3898111abd00e8835e
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

Loading…