Ammonium Hydroxide → 1-Fluoro-4-hydroxycarbazole

HRID 2119833Notes

Reaction equation

HRID 2119833 reaction equation
[F:1][C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[C:5]([O:15]C)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1.[OH-].[NH4+]>>[F:1][C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[C:5]([OH:15])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 10176127Pyridinium chlorideHCID 221477961-Fluoro-4-methoxycarbazole

Product 1

HCID 221478201-Fluoro-4-hydroxycarbazoleYield 114.5%

Procedure

A mixture of 1-fluoro-4-methoxycarbazole (438 mg, 2.04 mmol) and pyridine hydrochloride (3 g) was placed into an oil bath that was preheated to 220° C. After 20 minutes, the reaction was poured onto a mixture of ice and concentrated ammonium hydroxide. The product was extracted into ethyl acetate and the extract was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was azeotroped with toluene to give 470 mg of the title compound. Yield: >100%. MS(FD).

Workup

  1. customwas placed into an oil bath
  2. customwas preheated to 220° C
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialthe extract was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-1284a901b4c64ca4a9bbf5bd5c8d839d
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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