Isopropanol → HCID 9927687, compound

HRID 1884140Notes

Reaction equation

HRID 1884140 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N:17]1C(C)=[CH:20][CH:19]=[C:18]1C.[OH-:24].[K+].Cl.N[OH:28].C[CH:30]([OH:32])C>O>[CH3:30][O:32][C:20](=[O:28])[CH2:19][C:18]([NH:17][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:7][C:2]=1[F:1])=[O:24]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 22137973HCID 22137973, compound

Product 1

HCID 9927687HCID 9927687, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of the 1-[2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-2,5-dimethyl-1H-pyrrole (23.7 g, 76 mmol), potassium hydroxide (8.5 g, 151 mmol), hydroxylamine HCl (62.5 g, 899 mmol) in water (125 mL) and propan-2-ol (250 mL) was heated at 100° C. for 36 h. After cooling to room temperature, the mixture was poured into water, and extracted with diethylether. The combined organic layers were then washed with brine, dried and the resulting solution was diluted with HCl in diethylether. The resulting precipitate was then filtered off to afford the title compound (15.2 g, 74%) as a light brown solid. MS: m/e=236.0 (M+−Cl).

Workup

  1. extractionextracted with diethylether
  2. washThe combined organic layers were then washed with brine
  3. customdried
  4. additionthe resulting solution was diluted with HCl in diethylether
  5. filtrationThe resulting precipitate was then filtered off

Sources & evidence

ORD record
ord-dbc8d73eb0d24e7d912b5f1ad488582b
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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