Lithium Chloride → HCID 18671656, compound

HRID 1057646Notes

Reaction equation

HRID 1057646 reaction equation
[CH2:1]([N:8]1[C:20]2[CH2:19][CH2:18][C:17](Cl)([Cl:21])[C:16](=[O:23])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[Cl-]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([Cl:21])=[C:16]([OH:23])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 18671661HCID 18671661, compound

Product 1

HCID 18671656HCID 18671656, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 9-benzyl-3,3-dichloro-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.225 g, 1.78 mmol), LiCl (0.225 g, 5.34 mmol), Li2CO3 (0.395 g, 5.34 mmol), and DMF (6 mL) is heated at 135° C. for 45 min. After cooling, the mixture is partitioned between ethyl ether and aq. ammonium chloride/brine and brine. The organic layer is dried over magnesium sulfate and concentrated to dryness. Chromatography on silica gel (40 mL) using ethyl acetate/hexane (10/90) gave 0.382 g of 9-benzyl-3-chloro-9H-carbazol-4-ol. 1H NMR (CDCl3) δ5.48, 6.14, 6.88, 7.11, 7.12, 7.24-7.36, 7.43, 8.37.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between ethyl ether and aq. ammonium chloride/brine and brine
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8478ec8f9cb9432f853b419e9f2b4b43
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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