Water → HCID 18968756, compound

HRID 398778Notes

Reaction equation

HRID 398778 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([Cl:10])=[O:9].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)[CH:16]=1.O>C(O)(C)C>[ClH:10].[F:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([C:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:21]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)[CH:22]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 98082-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 134903481-(pyridin-3-yl)-1H-indole

Product 1

HCID 18968756HCID 18968756, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred mixture of 58 g. (0.93 mole) of aluminum chloride in 240 ml. of MDC was added a solution of 28.6 g. (0.18 mole) of 2-fluorobenzoyl chloride in 100 ml. of MDC. The resulting mixture was stirred for two hours and then added dropwise to a solution of 29 g. (0.149 mole) of 1-(3-pyridinyl)-1H-indole in 200 ml. of MDC. When addition was complete the reaction mixture was stirred for fifteen minutes and then poured into 1 liter of water. The organic layer was separated, washed with aqueous sodium bicarbonate, dried over magnesium sulfate and taken to dryness in vacuo to give 50 g. of a red oil. The latter was dissolved in 200 ml. of isopropanol, the solution was treated with 10 ml. of concentrated hydrochloric acid, and the solid which separated was collected and dried to give 24.8 g. of product which was recrystallized from ethanol to give 3-(2-fluorobenzoyl)-1-(3-pyridinyl)-1H-indole hydrochloride, m.p. 205°-212° C.

Workup

  1. additionTo a stirred mixture of 58 g
  2. additionof MDC was added a solution of 28.6 g
  3. additionadded dropwise to a solution of 29 g
  4. additionWhen addition
  5. stirringwas stirred for fifteen minutes
  6. customThe organic layer was separated
  7. washwashed with aqueous sodium bicarbonate
  8. dry with materialdried over magnesium sulfate
  9. customto give 50 g
  10. dissolutionThe latter was dissolved in 200 ml
  11. customof concentrated hydrochloric acid, and the solid which separated
  12. customwas collected
  13. customdried
  14. customto give 24.8 g
  15. customof product which was recrystallized from ethanol

Sources & evidence

ORD record
ord-a824afaa0c644bbab1e6e9a12d244c16
Source dataset
uspto-grants-1998_10
Patent number
US05817651

Reaction notes

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