Water → HCID 69235228, compound

HRID 1593630Notes

Reaction equation

HRID 1593630 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:15]([NH2:17])=O)[CH2:6][C:5]2=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([CH2:15][NH2:17])[CH2:6][C:5]2=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 69236439HCID 69236439, compound

Product 1

HCID 69235228HCID 69235228, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6-Chloro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid amide (0.6 g, 2.42 mmole) was dissolved in THF (20 ml). The reaction was cooled to 0° C. Lithium aluminum hydride (4.8 ml, 1M, 4.8 mmole) was portion wise carefully added. The reaction was refluxed for 2 hours. After cooling the mixture to room temperature water was carefully drop wise added to deactivate the Li—Al-complex. The formed solids were filtered and the filtrate diluted with ethyl acetate, washed with water (2×), brine and the separated organic layer dried over magnesium sulfate, filtered and evaporated in vacuo. The product was crystallized from ethyl acetate/hexane, 80:20. A white solid was obtained, 0.293 g, 52% yield. mp. 142-144° C. MS: ES [M−H]− 233.1.

Workup

  1. additionwise carefully added
  2. temperatureThe reaction was refluxed for 2 hours
  3. additionwas carefully drop wise added
  4. filtrationThe formed solids were filtered
  5. additionthe filtrate diluted with ethyl acetate
  6. washwashed with water (2×), brine
  7. dry with materialthe separated organic layer dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe product was crystallized from ethyl acetate/hexane, 80:20
  11. customA white solid was obtained

Sources & evidence

ORD record
ord-58a198ad88dd4c25a77c5d868c479eda
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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