Water → HCID 18993183, compound

HRID 375630Notes

Reaction equation

HRID 375630 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[CH2:24][C:25]([Cl:27])=[O:26].O>O1CCOCC1.CCOCC>[Cl:27][C:25](=[O:26])[CH2:24][C:12]1[C:11]2[C:15](=[CH:16][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)[NH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 111066586-(4-FLUOROPHENYL)INDOLE

Product 1

HCID 18993183HCID 18993183, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution under N2 of 6-(4-fluorophenyl)indole (10.0 g, 47.4 mmol), prepared as described in WO 93/01813, in dioxane (36 mL) and pyridine (5.8 mL, 71.8 mmol) was heated to 60° C. and a solution of chloroacetyl chloride (5.7 mL, 71.1 mmol) in dioxane (12.5 mL) was added dropwise over 1 hour. The reaction mixture was stirred for 1 hour at 60° C., then cooled to ambient temperature and poured into a mixture of H2O (200 mL) and ether (50 mL). The resulting orange precipitate was filtered and dried. Recrystallization from ethanol, followed by rinsing with cold ether gave 1-chloro-2-[6-(4-fluorophenyl)indol-3-yl]ethanone (2.8 g) as an orange solid.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe resulting orange precipitate was filtered
  3. customdried
  4. customRecrystallization from ethanol
  5. washby rinsing with cold ether

Sources & evidence

ORD record
ord-04ddf92a4e4a46f881641e8066cd592d
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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